methyl 3-cyclopenta-1,4-dienylacetate | 37455-98-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 3-cyclopenta-1,4-dienylacetate
• 英文别名: methyl 2,4-cyclopentadiene-1-acetate；2,4-Cyclopentadienyl acetic acid methyl ester；(Cyclopenta-1,3-dien-5-yl)-essigsaeure-methylester；Methyl 2,4-cyclopentadien-1-ylacetate；methyl 2-cyclopenta-2,4-dien-1-ylacetate
• CAS: 37455-98-4
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: YPDLBHGTHWIARC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 3-cyclopenta-1,4-dienylacetate 在 (+)-二异松蒎烯基硼烷 、 双氧水 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 22.5h， 以31%的产率得到(-)-trans-2-methoxycarbonylmethylcyclopent-3-en-1-ol
  参考文献：
  名称：

  ASYMMETRIC HYDROBORATION OF 5-SUBSTITUTED CYCLOPENTADIENES: SYNTHESIS OF METHYL (1 R,5R)-5-HYDROXY-2-CYCLOPENTENE-1-ACETATE

  摘要：

  DOI：

  10.15227/orgsyn.063.0044
• 作为产物：
  描述：

  dicyclopentadiene 在 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 methyl 3-cyclopenta-1,4-dienylacetate
  参考文献：
  名称：

  ASYMMETRIC HYDROBORATION OF 5-SUBSTITUTED CYCLOPENTADIENES: SYNTHESIS OF METHYL (1 R,5R)-5-HYDROXY-2-CYCLOPENTENE-1-ACETATE

  摘要：

  DOI：

  10.15227/orgsyn.063.0044

文献信息

• [(η-C5H4R)Fe(CO)2X], X = Cl, Br, I, NO3, CO2Me and [(η-C5H4R)Fe(CO)3]+, R = (CH2)nCO2Me (n = 0–2), and CO2CH2CH2OH: a new group of CO-releasing molecules
  作者：David Scapens、Harry Adams、Tony R. Johnson、Brian E. Mann、Philip Sawle、Rehan Aqil、Trevor Perrior、Roberto Motterlini

  DOI：10.1039/b704832g

  日期：——

  A new group of CO-releasing molecules, CO-RMs, based on cyclopentadienyl iron carbonyls have been identified. X-Ray structures have been determined for [(η-C5H4CO2Me)Fe(CO)2X], X = Cl, Br, I, NO3, CO2Me, [(η-C5H4CO2Me)Fe(CO)2]2, [(η-C5H4CO2CH2CH2OH)Fe(CO)2]2 and [(η-C5H4CO2Me)Fe(CO)3][FeCl4]. Half-lives for CO release, 1H, 13C, and 17OC NMR and IR spectra have been determined along with some biological data for these compounds, [(η-C5H4CO2CH2CH2OH)Fe(CO)3]+ and [η-C5H4(CH2)nCO2Me}Fe(CO)3]+, n = 1, 2. More specifically, cytotoxicity assays and inhibition of nitrite formation in stimulated RAW264.7 macrophages are reported for most of the compounds analyzed. [(η-C5H5)Fe(CO)2X], X = Cl, Br, I, were also examined for comparison. Correlations between the half-lives for CO release and spectroscopic parameters are found within each group of compounds, but not between the groups.

  一组基于环戊二烯基铁碳基化合物的新型释放一氧化碳分子（CO-RMs）已被确认。已确定[(η- CO2Me)Fe(CO)2X]的X射线结构，其中X包括Cl、Br、I、NO3、CO2Me，及[(η- CO2Me)Fe(CO)2]2、[(η- CO2 OH)Fe(CO)2]2和[(η- CO2Me)Fe(CO)3][FeCl4]。这些化合物的CO释放半衰期、1H、13C和17OC NMR以及红外光谱已被确定，并提供了一些生物数据，包括[(η- CO2 OH)Fe(CO)3]+和[η-C5H4(CH2)nCO2Me}Fe(CO)3]+（n = 1, 2）。更具体地说，针对大多数分析化合物，在刺激的RAW264.7巨噬细胞中进行了细胞毒性实验和亚硝酸盐形成抑制实验。此外，还对[(η-C5H5)Fe(CO)2X]（X = Cl、Br、I）进行了比较研究。在每组化合物中，CO释放的半衰期与光谱参数之间存在相关性，但不同组之间则没有。
• [EN] METHOD AND MOLECULES<br/>[FR] MÉTHODE ET MOLÉCULES
  申请人：MEDIMMUNE LLC

  公开号：WO2018218093A1

  公开（公告）日：2018-11-29

  The present invention provides a bioconjugation method and compounds for use therein. The bioconjugation method comprises the step of conjugating a biological molecule containing a first unsaturated functional group with a payload comprising a second unsaturated functional group, wherein the first and second unsaturated functional groups are complementary to each other such that conjugation is a reaction of said functional groups via a Diels-Alder reaction which forms a cyclohexene ring.

  本发明提供了一种生物共轭方法和其中使用的化合物。该生物共轭方法包括将含有第一不饱和官能团的生物分子与包含第二不饱和官能团的荷载物质共轭的步骤，其中第一和第二不饱和官能团互补，使得通过 Diels-Alder 反应发生官能团之间的结合，形成一个环己烯环。
• Asymmetric synthesis of optically active prostaglandins
  申请人：Hoffmann-La Roche Inc.

  公开号：US03933892A1

  公开（公告）日：1976-01-20

  An asymmetric synthesis of optically active prostaglandin F.sub.2.sub..alpha. from cyclopentadiene including intermediates in this synthesis.

  从环戊二烯中对光学活性前列腺素F.sub.2.sub..alpha.进行不对称合成，包括在合成过程中的中间体。
• Prostanoic acid derivatives
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04210669A1

  公开（公告）日：1980-07-01

  Prostanoic acid derivatives of the formula, ##STR1## wherein R.sub.1 is hydrogen or C.sub.1-4 alkyl, R.sub.2 is C.sub.4-8 alkyl and >C.dbd.Z is >C.dbd.0 or ##STR2## are prepared by reacting a cyclopentane of the formula, ##STR3## wherein R.sub.2 is defined above and R is hydrogen or tetrahydropyranyl, with Wittig reagent of the formula, (R.sub.3).sub.3 P.dbd.CH(CH.sub.2).sub.3 COOM wherein R.sub.3 is aryl and M is alkali metal and, if necessary, hydrolyzing, or by oxidizing a compound of the formula, ##STR4## wherein R.sub.1 and R.sub.2 are as defined above and R.sub.9 is tetrahydropyranyl group, with an oxidizing agent. The compounds (I) are useful as anti-ulcer agent.

  本发明涉及一种公式为##STR1##的前列腺酸衍生物，其中R.sub.1为氢或C.sub.1-4烷基，R.sub.2为C.sub.4-8烷基，>C.dbd.Z为>C.dbd.0或##STR2##，其制备方法为将公式为##STR3##的环戊烷（其中R.sub.2如上所述，R为氢或四氢吡喃基）与Wittig试剂（公式为(R.sub.3).sub.3 P.dbd.CH(CH.sub.2).sub.3 COOM，其中R.sub.3为芳基，M为碱金属），必要时水解，或者通过氧化公式为##STR4##的化合物（其中R.sub.1和R.sub.2如上所述，R.sub.9为四氢吡喃基）与氧化剂反应制得。该化合物（I）可用作抗溃疡剂。
• Cyclopentylacetic acid derivatives
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04233222A1

  公开（公告）日：1980-11-11

  Prostanoic acid derivatives of the formula, ##STR1## wherein R.sub.1 is hydrogen or C.sub.1-4 alkyl, R.sub.2 is C.sub.4-8 alkyl and >C=Z is >C=O or ##STR2## are prepared by reacting a cyclopentane of the formula, ##STR3## wherein R.sub.2 is defined above and R is hydrogen or tetrahydropyranyl, with Wittig reagent of the formula, (R.sub.3).sub.3 P.dbd.CH(CH.sub.2).sub.3 COOM wherein R.sub.3 is aryl and M is alkali metal and, if necessary, hydrolyzing, or by oxidizing a compound of the formula, ##STR4## wherein R.sub.1 and R.sub.2 are as defined above and R.sub.9 is tetrahydropyranyl group, with an oxidizing agent. The compounds (I) are useful as anti-ulcer agent.

  本发明涉及一种公式为##STR1##的前列腺酸衍生物，其中R.sub.1为氢或C.sub.1-4烷基，R.sub.2为C.sub.4-8烷基，>C=Z为>C=O或##STR2##。该衍生物可通过将公式为##STR3##的环戊烷（其中R.sub.2如上所定义，R为氢或四氢吡喃基）与公式为(R.sub.3).sub.3 P.dbd.CH(CH.sub.2).sub.3 COOM的Wittig试剂（其中R.sub.3为芳基，M为碱金属），必要时水解，或通过氧化公式为##STR4##的化合物（其中R.sub.1和R.sub.2如上所定义，R.sub.9为四氢吡喃基）而制备。该化合物（I）可用作抗溃疡剂。