(1S,6R)-8,8-dichlorobicyclo<4.2.0>oct-2-en-7-one | 115224-50-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,6R)-8,8-dichlorobicyclo<4.2.0>oct-2-en-7-one
• 英文别名: (1S,6R)-8,8-dichlorobicyclo[4.2.0]oct-2-en-7-one
• CAS: 115224-50-5
• 化学式: C₈H₈Cl₂O
• 分子量: 191.057
• InChiKey: MHFJPIZWTIKAND-RITPCOANSA-N

物化性质

• 沸点：
  288.1±40.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,6R)-8,8-dichlorobicyclo<4.2.0>oct-2-en-7-one 生成 bicyclo<4.2.0>oct-2-en-7-one
  参考文献：
  名称：

  KERTESZ, DENIS J.;KLUGE, ARTHUR F., J. ORG. CHEM., 53,(1988) N 21, C. 4962-4968

  摘要：

  DOI：
• 作为产物：
  描述：

  (1S,6R,7R)-8,8-dichlorobicyclo[4.2.0]oct-2-en-7-ol 生成 (1S,6R)-8,8-dichlorobicyclo<4.2.0>oct-2-en-7-one
  参考文献：
  名称：

  KERTESZ, DENIS J.;KLUGE, ARTHUR F., J. ORG. CHEM., 53,(1988) N 21, C. 4962-4968

  摘要：

  DOI：

文献信息

• Process and intermediates for the synthesis of the enantiomers of bicyclo(4.2.0)oct-2-en-7-one and derivatives and for the synthesis of bicyclo(4.2.0)octane derivatives
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0257610A3

  公开（公告）日：1989-05-24

  The enantiomers of formulas are prepared in a sequence starting from the racemic compound of formulawherein X is hydrogen or bromo when Y is bromo, or X is chloro when Y is chloro.The key step of this process involves a microbial reduction of the compound of formula (3) to give a ketone and an alcohol of high enantiomeric purity. The compounds of formulas (1) and (2) are intermediates for the preparation of certain bicyclo[4.2.0]octane derivatives.

  这些公式的对映异构体是从公式的消旋化合物开始的顺序制备的，其中X为氢或溴，Y为溴时，或者X为氯，Y为氯时。这个过程的关键步骤涉及将公式（3）的化合物进行微生物还原，得到高对映纯度的酮和醇。公式（1）和（2）的化合物是制备某些双环[4.2.0]辛烷衍生物的中间体。
• Novel substituted (4.2.0)bicyclooctane derivatives with valuable
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04735966A1

  公开（公告）日：1988-04-05

  Compounds useful in treating cardiovascular disorders such as thrombosis, hypertension and atherosclerosis are depicted in formulas (1), (2) and (3): ##STR1## wherein: A is --C.tbd.C--, trans --HC.dbd.CH--, --CH.sub.2 CH.sub.2 -- or --CH.dbd.CHCH.sub.2 --; X is lower alkoxy, hydroxy, or (2,2,2)-trifluoroethoxy; Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl); is an integer of 2-4; R.sub.1 is --CH.sub.2 OH, --CHO, --CO.sub.2 R or --CO.sub.2 H, and the olefin formed by the R.sub.1 (CH.sub.2).sub.n CH.dbd. moiety is either (E) or (Z); R.sub.2 is hydrogen or methyl, or optionally --CH.dbd.CH.sub.2 when A is --CH.dbd.CHCH.sub.2 --; and R.sub.3 is linear or branched alkyl, alkenyl or alkynyl having 5-10 carbon atoms, ##STR2## --(CH.sub.2).sub.m -phenyl or CH.sub.2 O-phenyl; in which each phenyl may be optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen; in which: a is an integer of 0, 1 or 2; b is an integer of 3-7; m is an integer of 0, 1 or 2; and R is ##STR3## wherein x is ##STR4## in which each R.sub.4 is independently hydrogen or lower alkyl having 1-6 carbon atoms, and the pharmaceutically acceptable, non-toxic salts and esters thereof.

  化合物(1)、(2)和(3)中描绘了用于治疗心血管疾病如血栓形成、高血压和动脉粥样硬化的有用化合物的结构式：其中：A为--C.tbd.C--、顺式--HC.dbd.CH--、--CH.sub.2 CH.sub.2 --或--CH.dbd.CHCH.sub.2 --；X为较低的烷氧基、羟基或(2,2,2)-三氟乙氧基；Y为氢、外侧-(较低烷基)或内侧-(较低烷基)；n为2-4的整数；R.sub.1为--CH.sub.2 OH、--CHO、--CO.sub.2 R或--CO.sub.2 H，由R.sub.1 (CH.sub.2).sub.n CH.dbd.部分形成的烯烃为(E)或(Z)；R.sub.2为氢或甲基，或当A为--CH.dbd.CHCH.sub.2 --时，可选地为--CH.dbd.CH.sub.2；R.sub.3为线性或支链烷基、烯基或炔基，具有5-10个碳原子，##STR2## --(CH.sub.2).sub.m -苯基或CH.sub.2 O-苯基；其中每个苯基可以可选地被较低烷基、较低烷氧基、三氟甲基或卤素取代；其中：a为0、1或2的整数；b为3-7的整数；m为0、1或2的整数；R为##STR3## 其中x为##STR4## 其中每个R.sub.4独立地为氢或具有1-6个碳原子的较低烷基，以及其药用可接受的、非毒性的盐和酯。
• Novel processes for the synthesis of certain bicyclo(4.2.0)octane
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04927963A1

  公开（公告）日：1990-05-22

  A process for preparing compounds represented by the formula ##STR1## wherein: X is hydrogen or lower alkoxy; Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl); n is an integer from 2-4; R.sub.2 is hydrogen or methyl; and R.sub.3 is linear or branched alkyl, ##STR2## --(CH.sub.2).sub.m -phenyl or --CH.sub.2 O-phenyl; in which any phenyl may be optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen, and a is an integer of 0, 1 or 2; b is an integer of 3-7; m is an integer of 0, 1 or 2, as a mixture or separately in a sequence starting from an epoxide represented by the formula ##STR3## and processes for making the novel intermediates.

  一种制备化合物的方法，该化合物由以下式子表示：##STR1## 其中：X是氢或低级烷氧基；Y是氢，外-（低级烷基）或内-（低级烷基）；n是2-4的整数；R.sub.2是氢或甲基；R.sub.3是线性或支链烷基，##STR2## --（CH.sub.2）.sub.m-苯基或--CH.sub.2 O-苯基；其中任何苯基均可选择性地用低级烷基，低级烷氧基，三氟甲基或卤素取代，a是0、1或2的整数；b是3-7的整数；m是0、1或2的整数，作为混合物或单独序列的形式，从由以下式子表示的环氧化物开始：##STR3## 并且制备新的中间体的方法。
• Novel process for the synthesis of the enantiomers of
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05049497A1

  公开（公告）日：1991-09-17

  The enantiomers of formulas ##STR1## are prepared in a sequence starting from the racemic compound of formula ##STR2## wherein X is hydro or bromo when Y is bromo, or X is chloro when Y is chloro. The key step of this process involves a microbial reduction of the compound of formula (3) to give a ketone and an alcohol of high enantiomeric purity.

  公式##STR1##的对映异构体是通过从公式##STR2##的消旋化合物开始的序列制备的，其中当Y为溴时，X为氢或溴，或者当Y为氯时，X为氯。该过程的关键步骤涉及将公式（3）的化合物进行微生物还原，以得到高对映纯度的酮和醇。
• Novel substituted (4.2.0)Bicyclooctane derivatives with valuable therapeutic properties
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0257609A2

  公开（公告）日：1988-03-02

  Compounds useful in treating cardiovascular disorders such as thrombosis, hypertension and atherosclerosis , in inhibiting gastric acid secretion and in preventing and treating peptic and intestinal ulcers, are depicted in formulas (1), (2) and (3) : wherein: A is -C≡C-, trans -HC = CH-, -CH2CH2-or -CH=CHCH2-; X is lower alkoxy, hydroxy, or (2,2,2)-trifluoroethoxy; Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl); n is an integer of 2-4; R1 is -CH2OH, -CHO, -CO2R or -COzH, and the olefin formed by the R1(CHz) nCH = moiety is either (E) or (Z); R2 is hydrogen or methyl, or optionally -CH = CH2 when A is -CH = CHCHr; and R3 is linear or branched alkyl, alkenyl or alkynyl having 5-10 carbon atoms, , -(CH2)m -phenyl or CH2O-phenyl; in which each phenyl may be optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen; in which: a is an integer of 0, 1 or 2; b is an integer of 3-7; m is an integer of 0, 1 or 2; and R is wherein X is or in which each R4 is independently hydrogen or lower alkyl having 1-6 carbon atoms, and the pharmaceutically acceptable, non-toxic salts and esters thereof.

  可用于治疗心血管疾病（如血栓形成、高血压和动脉粥样硬化）、抑制胃酸分泌以及预防和治疗消化性溃疡和肠溃疡的化合物如式(1)、(2)和(3)所示： 其中 A 是-C≡C-、反式-HC = CH-、-CH2CH2-或-CH=CHCH2-； X 是低级烷氧基、羟基或 (2,2,2)-三氟乙氧基； Y 是氢、外-（低级烷基）或内-（低级烷基）； n 是 2-4 的整数； R1 是-CH2OH、-CHO、-CO2R 或-COzH，R1(CHz) nCH = 分子形成的烯烃是 (E) 或 (Z)； R2 是氢或甲基，或当 A 是-CH = CHCHr 时，任选为-CH = CH2；以及 R3 是具有 5-10 个碳原子的直链或支链烷基、烯基或炔基、 ，-(CH2)m-苯基或CH2O-苯基； 其中每个苯基可任选被低级烷基、低级烷氧基、三氟甲基或卤素取代； 其中：a 是 0、1 或 2 的整数； b 是 3-7 的整数 m 是 0、1 或 2 的整数；以及 R 是 其中 X 是 或 其中每个 R4 独立地为氢或具有 1-6 个碳原子的低级烷基，及其药学上可接受的无毒盐和酯。