2,3,4,8B-四氢-1ah-1-噁-苯并[a]环丙并[c]环庚烯 | 4443-71-4

• 分子结构分类: 有机化合物 - 苯类化合物
• 中文名称: 2,3,4,8B-四氢-1ah-1-噁-苯并[a]环丙并[c]环庚烯
• 英文名称: 1,2-epoxy-6,7,8,9-tetrahydro-5H-benzocycloheptene
• 英文别名: 3,4-benzo-1,2-epoxy-1,3-cycloheptadiene；3,4-epoxy-1,2-benzocyclohept-1-ene；1,2-epoxybenzosuberan；5,6-epoxy-6,7,8,9-tetrahydro-5H-benzocycloheptene；5,6-Epoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten；1a,3,4,8b-tetrahydro-2H-benzo[3,4]-cyclohept [1,2,b]oxirene；2,3,4,8b-Tetrahydro-1aH-1-oxa-benzo[a]cyclopropa[c]cycloheptene；3-oxatricyclo[6.4.0.02,4]dodeca-1(12),8,10-triene
• CAS: 4443-71-4
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: OHWMCUHFWPORRH-UHFFFAOYSA-N

物化性质

• 沸点：
  70-72 °C(Press: 0.2 Torr)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  2,3,4,8B-四氢-1ah-1-噁-苯并[a]环丙并[c]环庚烯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.5h， 以89%的产率得到1,2-Benzo-cycloheptenol-(4)
  参考文献：
  名称：

  结构对环苄基酮烯醇形成速率和稳定性的影响

  摘要：

  pKaK 值为 12.2 (la)、12.9 (lb) 和 14.9 (IC)。类似地，烯醇的酸解离常数随着环尺寸的增加而降低；pKaE 为 8.3 (Za)、9.2 (2b) 和 10.0 (2c)。烯醇化的平衡常数也随环大小而变化；pKE 值为 3.8 (la)、3.6 (lb) 和 4.9 (IC)。

  DOI：

  10.1021/ja00004a041
• 作为产物：
  描述：

  6,7,8,9-四氢-5H-苯并环庚烯-5-醇 在 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 27.0h， 生成 2,3,4,8B-四氢-1ah-1-噁-苯并[a]环丙并[c]环庚烯
  参考文献：
  名称：

  结构对环苄基酮烯醇形成速率和稳定性的影响

  摘要：

  pKaK 值为 12.2 (la)、12.9 (lb) 和 14.9 (IC)。类似地，烯醇的酸解离常数随着环尺寸的增加而降低；pKaE 为 8.3 (Za)、9.2 (2b) 和 10.0 (2c)。烯醇化的平衡常数也随环大小而变化；pKE 值为 3.8 (la)、3.6 (lb) 和 4.9 (IC)。

  DOI：

  10.1021/ja00004a041

文献信息

• HMG-CoA reductase inhibitors
  申请人：Stein Philip D.

  公开号：US20070249583A1

  公开（公告）日：2007-10-25

  Compounds are provided of the following structure are HMG CoA reductase inhibitors and thus are active in inhibiting cholesterol biosynthesis, modulating blood serum lipids, for example, lowering LDL cholesterol and/or increasing HDL cholesterol, and treating hyperlipidemia and dyslipidemia, hypercholesterolemia, hypertriglyceridemia and atherosclerosis wherein A is chosen from B is chosen from wherein the variables R 1 to R 7 , m, n, are as defined herein. A method for treating the above diseases employing the above compounds is also provided.

  提供以下结构的化合物是HMG CoA还原酶抑制剂，因此在抑制胆固醇生物合成、调节血清脂质，例如降低LDL胆固醇和/或增加HDL胆固醇，以及治疗高脂蛋白血症和血脂异常、高胆固醇血症、高甘油三酯血症和动脉粥样硬化方面具有活性。 其中A选择自 B选择自 其中变量R1至R7，m，n， 如本文所定义。 还提供了一种利用上述化合物治疗上述疾病的方法。
• Nucleophilic ring opening of epoxides by carbanions
  作者：A. Chatterjee、D. Banerjee、B. Banerjee、R. Mallik

  DOI：10.1016/s0040-4020(01)92158-1

  日期：——

  different steric requirements under refluxing benzene afforded a single stereoisomer of the cyclopropane derivatives 4. The same reaction under refluxing ethanol gave the normal products, i.e. the trans-lactones 6. Mechanism and high stereoselectivity observed in the novel cyelopropane formation, and regiospecific cleavage of the cyclopropane carboxylic acids (in4) have also been discussed in detail

  在回流的苯下，具有不同空间要求的碳环的环氧化物2（ad）的亲核性开环提供了环丙烷衍生物4的单一立体异构体。在回流的乙醇下进行相同的反应，得到正常产物，即反式内酯6。还详细讨论了在新的环丙烷形成中观察到的机理和高立体选择性，以及环丙烷羧酸的区域特异性裂解（图4）。
• Benzocyclohexanes and benzocycloheptanes useful as analgesics
  申请人：Roussel Uclaf

  公开号：US05130329A1

  公开（公告）日：1992-07-14

  Novel all possible enantiomeric and diastereoisomeric forms of compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, halogen, alkyl and alkoxy of 1 to 5 carbon atoms, --No.sub.2, --NH.sub.2 and mono and dialkylamino of 1 to 5 alkyl carbon atoms, A and B have the trans configuration, one of A and B being ##STR2## R.sub.2 is hydrogen or alkyl of 1 to 5 carbon atoms, Z is --(CH.sub.2).sub.n2, n.sub.2 being an integer from 0 to 5 or branched alkylene of 2 to 8 carbon atoms or --CH.sub.2 --O--, Y is selected from the group consisting of phenyl, naphthyl, indenyl, heteromonocycle of 5 to 6 ring atoms and heterobicycle, all optionally having at least one substituent and the other of A and B is ##STR3## R.sub.4 and R.sub.5 individually being selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms or taken together with the nitrogen to which they are attached form a 5 to 6 ring heterocycle optionally containing a heteroatom selected from the group consisting of --O--, --S-- and --NH-- and their non-toxic, pharmaceutically acceptable acid addition salts having central analgesic properties and a strong affinity for opiate receptors.

  本发明涉及化合物的所有可能的对映体和二对映异构体形式，其化学式为##STR1##其中R.sub.1从氢、卤素、1到5个碳原子的烷基和烷氧基、--No.sub.2、--NH.sub.2和1到5个碳原子的单烷基和双烷基氨基中选择，A和B具有反构型，A和B中的一个为##STR2##R.sub.2为氢或1到5个碳原子的烷基，Z为--(CH.sub.2).sub.n2，n.sub.2为0到5的整数或2到8个碳原子的支链烷基或--CH.sub.2--O--，Y从苯基、萘基、茚基、5到6个环原子的杂环和杂环中选择，所有这些基团可选择地至少有一个取代基，A和B中的另一个为##STR3##R.sub.4和R.sub.5分别从氢和1到5个碳原子的烷基中选择，或者与它们连接的氮原子一起形成一个5到6环杂环，该杂环可选择地包含从--O--、--S--和--NH--中选择的杂原子，并且它们的无毒、药学上可接受的酸盐具有中枢镇痛特性和对阿片受体的强亲和力。
• Production method of optically active epoxy compound, complex used for the method and production method of the complex
  申请人：Kondo Shoichi

  公开号：US20080234502A1

  公开（公告）日：2008-09-25

  [Problem] To provide a production method of optically active epoxy compound, and a complex used for the production method and a production method of the complex. [Means for solving the problem] The skeleton that is necessary for expressing a high catalyst activity of optically active titanium salan complex of formulae (1) and (1′) and the substituent that is useful therefor and the position of the substituent are identified, and it is found that optically active epoxy compounds can be produced with a high enantioselectivity and a high chemical yield compared with a case where the prior optically active titanium salan complex is used. The production method comprises subjecting a prochiral compound (formula (4), (5) or (6)) having carbon-carbon double bond in the molecule to asymmetric epoxidation to produce an optically active epoxy compound (formula (7), (8) or (9)). The present invention relates also to a complex used for the production method and a production method of the complex.

  [问题] 提供一种光学活性环氧化合物的生产方法，以及用于该生产方法的复合物和复合物的生产方法。 [解决问题的方法] 确定表达式（1）和（1'）的光学活性钛萨兰配合物具有高催化活性所必需的骨架和有用的取代基及其位置，并发现与使用先前的光学活性钛萨兰配合物相比，可以以高对映选择性和高化学收率生产光学活性环氧化合物。该生产方法包括将具有分子中碳-碳双键的非手性化合物（式（4），（5）或（6））经过不对称环氧化反应，产生光学活性环氧化合物（式（7），（8）或（9））。本发明还涉及用于生产方法的复合物和复合物的生产方法。
• Benzocyclohexanes and analgesic compositions thereof
  申请人：Roussel Uclaf

  公开号：US05068244A1

  公开（公告）日：1991-11-26

  Novel all possible enantiomeric and diastereoisomeric forms of compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, halogen, alkyl and alkoxy of 1 to 5 carbon atoms, --NO.sub.2, --NH.sub.2 and mono and dialkylamino of 1 to 5 alkyl carbon atoms, n is 1 or 2, A and B have the trans configuration, one of A and B being ##STR2## R.sub.2 is hydrogen or alkyl of 1 to 5 carbon atoms, Z is --(CH.sub.2)--.sub.n2, n.sub.2 being an integer from 0 to 5 or branched alkylene of 2 to 8 carbon atoms or --CH.sub.2 --O--, Y is selected from the group consisting of phenyl, naphthyl, indenyl, heteromonocycle of 5 to 6 ring atoms and heterobicycle, all optionally having at least one substituent and the other of A and B is ##STR3## R.sub.4 and R.sub.5 individually being selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms or taken together with the nitrogen to which they are attached form a 5 to 6 ring heterocycle optionally containing a heteroatom selected from the group consisting of --O--, --S-- and --NH-- with the proviso 1) A is ##STR4## wherein R.sub.4 l and R.sub.5 have the above definitions and B is ##STR5## wherein R.sub.2, Z and Y have the above definition or 2) Z is --(CH.sub.2).sub.n2 -- and n.sub.2 is 0,2,3,4 or 5 or branched alkylene of 2 to 8 carbon atoms or --CH.sub.2 O-- yr 3) Y is phenyl substituted with at least one member of the group consisting of alkyl of 1 to 5 carbon atoms, alkoxy of 2 to 5 carbon atoms, --NH.sub.2 and mono and dialkylamino or 4) Y is naphthyl, indenyl, heteromonocycle of 5 to 6 ring atoms or heterobicycle, all optionally substituted with at least one substituent, except unsubstituted benzothiophene or 5) R.sub.1 is --NO.sub.2 or 6) R.sub.2 is alkyl of 4 to 5 carbon atoms or 7) R.sub.1 is hydrogen, n.sub.1 is 1, A is ##STR6## Y is selected from the group consisting of 3,4-dimethoxy-phenyl, 4-nitro-phenyl and benzothienyl and B is pyrrolidinyl or 8) R.sub.1 is hydrogen, n.sub.1 is 2, A is ##STR7## Y is selected from the group consisting of 3,4-dimethoxy-phenyl, 3,4-dichloro-phenyl, 4-trifluoromethyl-phenyl, 4-nitro-phenyl and benzothienyl and B is pyrrolidinyl and their non-toxic, pharmaceutically acceptable acid addition salts having central analgesic properties and a strong affinity for opiate receptors.

  本发明涉及一种化合物的所有可能的对映异构体和顺反异构体，该化合物的化学式为##STR1##其中R.sub.1选自氢、卤素、1至5个碳原子的烷基和烷氧基、--NO.sub.2、--NH.sub.2和1至5个烷基碳原子的单烷基和双烷基氨基，n为1或2，A和B具有反式构型，其中A和B中的一个为##STR2##R.sub.2为氢或1至5个碳原子的烷基，Z为--(CH.sub.2)--.sub.n2，n.sub.2为0至5的整数或2至8个碳原子的支链烷基或--CH.sub.2 --O--，Y选自苯基、萘基、茚基、5至6个环原子的杂环单环和杂环双环，所有这些都可以选择至少一个取代基，而A和B中的另一个为##STR3##其中R.sub.4和R.sub.5分别选自氢和1至5个碳原子的烷基，或与它们所连接的氮一起形成一个5至6个环的杂环，该杂环可以选择从--O--、--S--和--NH--中选择的一个杂原子，但是有以下规定：1）A为##STR4##其中R.sub.4和R.sub.5具有上述定义，B为##STR5##其中R.sub.2、Z和Y具有上述定义，或2）Z为--(CH.sub.2).sub.n2 --，n.sub.2为0、2、3、4或5或2至8个碳原子的支链烷基或--CH.sub.2 O--，或3）Y为至少有一个来自由1至5个碳原子的烷基、2至5个碳原子的烷氧基、--NH.sub.2和单烷基和双烷基氨基组成的群的取代基的苯基，或4）Y为萘基、茚基、5至6个环原子的杂环单环或杂环双环，所有这些都可以选择至少一个取代基，但不包括未取代的苯并噻吩，或5）R.sub.1为--NO.sub.2，或6）R.sub.2为4至5个碳原子的烷基，或7）R.sub.1为氢，n.sub.1为1，A为##STR6##Y选自3,4-二甲氧基苯基、4-硝基苯基和苯并噻吩，B为吡咯烷基，或8）R.sub.1为氢，n.sub.1为2，A为##STR7##Y选自3,4-二甲氧基苯基、3,4-二氯苯基、4-三氟甲基苯基、4-硝基苯基和苯并噻吩，B为吡咯烷基，以及它们的非毒性、药学上可接受的酸盐，具有中枢镇痛性和对阿片受体的强亲和力。