(3aR,5R,7aS)-methyl 2,2-dimethylhexahydrobenzo[d][1,3]dioxole-5-carboxylate | 1380226-21-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,5R,7aS)-methyl 2,2-dimethylhexahydrobenzo[d][1,3]dioxole-5-carboxylate
• 英文别名: methyl (3aR,5R,7aS)-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxole-5-carboxylate
• CAS: 1380226-21-0
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: CKBVDYBFSOSJRC-HRDYMLBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-氯苯甲酸甲酯 在 Escherichia coli JM₁₀₉ (pDTG₆₀₁A) 、 氢气 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (3aR,5R,7aS)-methyl 2,2-dimethylhexahydrobenzo[d][1,3]dioxole-5-carboxylate
  参考文献：
  名称：

  Toluene dioxygenase mediated oxidation of halogen-substituted benzoate esters

  摘要：

  一系列邻、间和对卤代甲基苯甲酸酯通过全细胞发酵与大肠杆菌JM109（pDTG601A）发生酶促二羟基化反应。只有邻取代的苯甲酸酯被代谢。2-氟苯甲酸甲酯产生一种二醇，而2-氯、2-溴和2-碘苯甲酸甲酯则分别产生一种区域异构体混合物。所有新代谢产物的绝对立体化学结构均已确定。对这些结果进行了计算分析，并提出了酶促二羟基化反应区域选择性的可能原理。

  DOI：

  10.1039/c2ob25202c

文献信息

• Toluene dioxygenase mediated oxidation of halogen-substituted benzoate esters
  作者：Vladislav Semak、Thomas A. Metcalf、Mary Ann A. Endoma-Arias、Pavel Mach、Tomas Hudlicky

  DOI：10.1039/c2ob25202c

  日期：——

  A series of ortho-, meta-, and para- halogen-substituted methyl benzoate esters was subjected to enzymatic dihydroxylation via the whole-cell fermentation with E. coli JM109 (pDTG601A). Only ortho-substituted benzoates were metabolized. Methyl 2-fluorobenzoate yielded one diol regioselectively whereas methyl 2-chloro-, methyl 2-bromo- and methyl 2-iodobenzoates each yielded a mixture of regioisomers. Absolute stereochemistry was determined for all new metabolites. Computational analysis of these results and a possible rationale for the regioselectivity of the enzymatic dihydroxylation is advanced.

  一系列邻、间和对卤代甲基苯甲酸酯通过全细胞发酵与大肠杆菌JM109（pDTG601A）发生酶促二羟基化反应。只有邻取代的苯甲酸酯被代谢。2-氟苯甲酸甲酯产生一种二醇，而2-氯、2-溴和2-碘苯甲酸甲酯则分别产生一种区域异构体混合物。所有新代谢产物的绝对立体化学结构均已确定。对这些结果进行了计算分析，并提出了酶促二羟基化反应区域选择性的可能原理。
• 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.