Methyl (1S,3S,4R)-3,4-dihydroxycyclohexane-1-carboxylate | 1062631-71-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl (1S,3S,4R)-3,4-dihydroxycyclohexane-1-carboxylate
• CAS: 1062631-71-3
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: SHNNPNZMDZPVLC-XVMARJQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl (1S,3S,4R)-3,4-dihydroxycyclohexane-1-carboxylate 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 Methyl (1S,3S,4R)-3,4-bis[(methanesulfonyl)oxy]cyclohexane-1-carboxylate
  参考文献：
  名称：

  Stereoselective synthesis and biological evaluation of 3,4-diaminocyclohexanecarboxylic acid derivatives as factor Xa inhibitors

  摘要：

  There have been few reports on synthetic methods for cis-1,2-diaminocyclohexane bearing a third ring substituent. Starting from 3-cyclohexenecarboxylic acid, we developed efficient methods for synthesizing the 3,4-diaminocyclohexanecarboxylic acid derivatives 2-5. We also evaluated their anti-Xa and anticoagulant activities. Among the compounds, acid 2a and amide 2b exhibited the most potent in vitro anti-fXa activity, indicating that the position and stereochemistry of a polar functional group on the cyclohexane ring greatly affected the in vitro anti-fXa activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.031
• 作为产物：
  描述：

  (3aR,5R,7aS)-methyl 2,2-dimethylhexahydrobenzo[d][1,3]dioxole-5-carboxylate 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 13.0h， 生成 Methyl (1S,3S,4R)-3,4-dihydroxycyclohexane-1-carboxylate
  参考文献：
  名称：

  Stereoselective synthesis and biological evaluation of 3,4-diaminocyclohexanecarboxylic acid derivatives as factor Xa inhibitors

  摘要：

  There have been few reports on synthetic methods for cis-1,2-diaminocyclohexane bearing a third ring substituent. Starting from 3-cyclohexenecarboxylic acid, we developed efficient methods for synthesizing the 3,4-diaminocyclohexanecarboxylic acid derivatives 2-5. We also evaluated their anti-Xa and anticoagulant activities. Among the compounds, acid 2a and amide 2b exhibited the most potent in vitro anti-fXa activity, indicating that the position and stereochemistry of a polar functional group on the cyclohexane ring greatly affected the in vitro anti-fXa activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.031

文献信息

• Stereoselective synthesis and biological evaluation of 3,4-diaminocyclohexanecarboxylic acid derivatives as factor Xa inhibitors
  作者：Tsutomu Nagata、Masatoshi Nagamochi、Shozo Kobayashi、Satoshi Komoriya、Toshiharu Yoshino、Hideyuki Kanno

  DOI：10.1016/j.bmcl.2008.07.031

  日期：2008.8

  There have been few reports on synthetic methods for cis-1,2-diaminocyclohexane bearing a third ring substituent. Starting from 3-cyclohexenecarboxylic acid, we developed efficient methods for synthesizing the 3,4-diaminocyclohexanecarboxylic acid derivatives 2-5. We also evaluated their anti-Xa and anticoagulant activities. Among the compounds, acid 2a and amide 2b exhibited the most potent in vitro anti-fXa activity, indicating that the position and stereochemistry of a polar functional group on the cyclohexane ring greatly affected the in vitro anti-fXa activity. (C) 2008 Elsevier Ltd. All rights reserved.