(1R,3S,4S)-4-chloro-3-hydroxycyclohexane-1-carboxylic acid | 76644-34-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: (1R,3S,4S)-4-chloro-3-hydroxycyclohexane-1-carboxylic acid
• CAS: 76644-34-3
• 化学式: C₇H₁₁ClO₃
• 分子量: 178.616
• InChiKey: MSTVTNQRWDYSNC-SRQIZXRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  cis-3,4-Epoxycyclohexanecarboxylic acid methyl ester 在 盐酸 、 氢氧化钾 作用下， 以 氯仿 为溶剂， 反应 12.5h， 生成 (1R,3S,4S)-4-chloro-3-hydroxycyclohexane-1-carboxylic acid
  参考文献：
  名称：

  Regiochemical control of the ring-opening of 1,2-epoxides by means of chelating processes. 2. Synthesis and reactions of the cis- and trans-oxides of 4-[(benzyloxy)methyl]cyclohexene, 3-cyclohexenemethanol, and methyl 3-cyclohexenecarboxylate

  摘要：

  The synthesis of the diastereoisomeric epoxides cis-1b-d and trans-2b-d and the products of their ring-opening by various nucleophiles are described. The results of the ring-openings of the trans-epoxides 2b-d can be rationalized by combining stereoelectronic and conformational arguments. However, the regioselectivity of the ring-openings of the cis-epoxides 1b-d can, in principle, be influenced by the chelation of a metal ion by the oxygen atom of the epoxy group and that of the substituent on the 4-position. The results of the reactions of the cis-epoxides 1b-d indicate that, to some degree, chelation is indeed a factor. How important a factor it is is dependent both on the reaction conditions and on the concentration and nature of the metal ion. In the ring-openings of the cis-epoxides 1b and 1d, chelation seems to be a larger factor than it is in the ring-openings of cis-epoxide 1c. However, in no case is chelation as large a factor as it was in the ring-openings of the cis-epoxide 1a, which was studied earlier. On the other hand, the autocatalyzed methanolysis, under neutral conditions, of epoxy acid 1e, followed by CH2N2 methylation of the crude product, afforded a mixture of the two regioisomeric hydroxy ethers in which the C-2-type compound predominates. This result suggests that intramolecular hydrogen bonding may determine the reactive conformation of 1e.

  DOI：

  10.1021/jo00031a018

文献信息

• PRODUCTION OF POLYKETIDES
  申请人：Buck Institute for Research on Aging

  公开号：EP1521828B1

  公开（公告）日：2015-07-01
• Production of polyketides and other natural products
  申请人：Biotica Technology Limited

  公开号：EP1589031B1

  公开（公告）日：2007-08-15
• PRODUCTION OF POLYKETIDES AND OTHER NATURAL PRODUCTS
  申请人：Gregory Alan Matthew

  公开号：US20080021211A1

  公开（公告）日：2008-01-24

  The present invention relates to production of polyketides and other natural products and to libraries of compounds and individual novel compounds. One important area is the isolation and potential use of novel FKBP-ligand analogues and host cells that produce these compounds. The invention is particularly concerned with methods for the efficient transformation of strains that produce FKBP analogues and recombinant cells in which cloned genes or gene cassettes are expressed to generate novel compounds such as polyketide (especially rapamycin) FKBP-ligand analogues, and to processes for their preparation, and to means employed therein (e.g. nucleic acids, vectors, gene cassettes and genetically modified strains).
• Production of Polyketides and Other Natural Products
  申请人：Gregory Matthew Alan

  公开号：US20080287482A1

  公开（公告）日：2008-11-20

  The present invention relates to production of polyketides and other natural products and to libraries of compounds and individual novel compounds. One important area is the isolation and potential use of novel FKBP-ligand analogues and host cells that produce these compounds. The invention is particularly concerned with methods for the efficient transformation of strains that produce FKBP analogues and recombinant cells in which cloned genes or gene cassettes are expressed to generate novel compounds such as polyketide (especially rapamycin) FKBP-ligand analogues, and to processes for their preparation, and to means employed therein (e.g. nucleic acids, vectors, gene cassettes and genetically modified strains).
• US7300942B2
  申请人：——

  公开号：US7300942B2

  公开（公告）日：2007-11-27