(3aα,5α,6α,7aα)-bis(phenylmethyl) (hexahydro-2,2-dimethyl-1,3-benzodioxole-5,6-diyl)bis(carbamate) | 135619-11-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3aα,5α,6α,7aα)-bis(phenylmethyl) (hexahydro-2,2-dimethyl-1,3-benzodioxole-5,6-diyl)bis(carbamate)
• 英文别名: benzyl N-[(3aS,5S,6R,7aR)-2,2-dimethyl-6-(phenylmethoxycarbonylamino)-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxol-5-yl]carbamate
• CAS: 135619-11-3
• 化学式: C₂₅H₃₀N₂O₆
• 分子量: 454.523
• InChiKey: IHBSGGXYYGFYIX-COPRSSIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  95.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aα,5α,6α,7aα)-bis(phenylmethyl) (hexahydro-2,2-dimethyl-1,3-benzodioxole-5,6-diyl)bis(carbamate) 在 palladium on activated charcoal 1,2,2,6,6-五甲基哌啶 、 盐酸 、 氢气 、 sodium hydride 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0~75.0 ℃ 、137.9 kPa 条件下， 反应 26.0h， 生成 (1α,2α,4β,5β)-4,4'-(4,5-dihydroxy-1,2-cyclohexanediyl)bis(2,6-piperazinedione)
  参考文献：
  名称：

  Syntheses and proton NMR conformational analyses of diastereomeric 4,4'-(4,5-dihydroxy-1,2-cyclohexanediyl)bis(2,6-piperazinedione)s and a synthetically related tricyclic octahydro-2,2-dimethyl-6-oxo-1,3-dioxolo[4,5-g]quinoxaline-5,8-diacetic acid ester

  摘要：

  Efficient syntheses for five of the six possible diastereoisomeric 4,4'-(4,5-dihydroxy-1,2-cyclohexanediyl)bis-(2,6-dioxopiperazine)s (5-9) and a synthetically related tricyclic 1,3-dioxolo[4,5-g]quinoxaline ring system 45 from their respective (4,5-dihydroxy-1,2-cyclohexanediyl)bis(carbamate)s 11-16 via isopropylidene-protected intermediates are described. Solution conformations of all targets and several synthetic intermediates in DMSO-d6 were determined using H-1 NMR and NOE methods, and the structure for polyheterocycle 45, obtained during attempted preparation of the sixth possible dioxopiperazine diastereomer 10, was determined with the additional aid of 2D COSY, 2D HETCOR, and H-1-C-13 correlation of long-range coupling (COLOC). Taken together, these studies provide evidence for the differences in reaction conditions required for bis(dioxopiperazine) synthesis, a relatively comprehensive analysis of dioxopiperazine and hydroxyl substituent effects on cyclohexane DMSO-d6 solution conformations, and a preliminary analysis of aqueous solubility differences.

  DOI：

  10.1021/jo00018a039
• 作为产物：
  描述：

  2-甲氧基丙烯 、 bis(phenylmethyl) (1α,2α,4β,5β)-(4,5-dihydroxy-1,2-cyclohexanediyl)bis(carbamate) 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 以88%的产率得到(3aα,5α,6α,7aα)-bis(phenylmethyl) (hexahydro-2,2-dimethyl-1,3-benzodioxole-5,6-diyl)bis(carbamate)
  参考文献：
  名称：

  Syntheses and proton NMR conformational analyses of diastereomeric 4,4'-(4,5-dihydroxy-1,2-cyclohexanediyl)bis(2,6-piperazinedione)s and a synthetically related tricyclic octahydro-2,2-dimethyl-6-oxo-1,3-dioxolo[4,5-g]quinoxaline-5,8-diacetic acid ester

  摘要：

  Efficient syntheses for five of the six possible diastereoisomeric 4,4'-(4,5-dihydroxy-1,2-cyclohexanediyl)bis-(2,6-dioxopiperazine)s (5-9) and a synthetically related tricyclic 1,3-dioxolo[4,5-g]quinoxaline ring system 45 from their respective (4,5-dihydroxy-1,2-cyclohexanediyl)bis(carbamate)s 11-16 via isopropylidene-protected intermediates are described. Solution conformations of all targets and several synthetic intermediates in DMSO-d6 were determined using H-1 NMR and NOE methods, and the structure for polyheterocycle 45, obtained during attempted preparation of the sixth possible dioxopiperazine diastereomer 10, was determined with the additional aid of 2D COSY, 2D HETCOR, and H-1-C-13 correlation of long-range coupling (COLOC). Taken together, these studies provide evidence for the differences in reaction conditions required for bis(dioxopiperazine) synthesis, a relatively comprehensive analysis of dioxopiperazine and hydroxyl substituent effects on cyclohexane DMSO-d6 solution conformations, and a preliminary analysis of aqueous solubility differences.

  DOI：

  10.1021/jo00018a039

文献信息

• Ethylenediamine derivatives
  申请人：——

  公开号：US20040122063A1

  公开（公告）日：2004-06-24

  The invention relates a compound represented by the formula (1): Q 1 -Q 2 -C(═O)—N(R 1 )-Q 3 -N(R 2 )-T 1 -Q 4 ( 1 ) wherein R 1 and R 2 represent H or the like; Q 1 represents an aromatic ring, heterocyclic ring or the like; Q 2 represents a single bond, aromatic ring, heterocyclic ring or the like; Q 3 represents a group 1 or the like, Q 4 represents an aromatic ring, heterocyclic ring or the like; and T 1 represents —CO— or —SO 2 —, and a medicine which comprises the compound and is useful for thrombosis and embolism.

  本发明涉及一种由式（1）表示的化合物：Q1-Q2-C(═O)—N(R1)-Q3-N(R2)-T1-Q4(1)，其中R1和R2代表H或类似物；Q1代表芳香环，杂环或类似物；Q2代表单键，芳香环，杂环或类似物；Q3代表群1或类似物，Q4代表芳香环，杂环或类似物；T1代表—CO—或—SO2—，以及包含该化合物并对治疗血栓和栓塞有用的药物。
• ETHYLENEDIAMINE DERIVATIVES
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP1270557B1

  公开（公告）日：2012-07-25
• Monoacylated 1,2-diaminocycloalkanes
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP2431370B1

  公开（公告）日：2013-06-19
• US7192968B2
  申请人：——

  公开号：US7192968B2

  公开（公告）日：2007-03-20
• Syntheses and proton NMR conformational analyses of diastereomeric 4,4'-(4,5-dihydroxy-1,2-cyclohexanediyl)bis(2,6-piperazinedione)s and a synthetically related tricyclic octahydro-2,2-dimethyl-6-oxo-1,3-dioxolo[4,5-g]quinoxaline-5,8-diacetic acid ester
  作者：Donald T. Witiak、Yong Wei

  DOI：10.1021/jo00018a039

  日期：1991.8

  Efficient syntheses for five of the six possible diastereoisomeric 4,4'-(4,5-dihydroxy-1,2-cyclohexanediyl)bis-(2,6-dioxopiperazine)s (5-9) and a synthetically related tricyclic 1,3-dioxolo[4,5-g]quinoxaline ring system 45 from their respective (4,5-dihydroxy-1,2-cyclohexanediyl)bis(carbamate)s 11-16 via isopropylidene-protected intermediates are described. Solution conformations of all targets and several synthetic intermediates in DMSO-d6 were determined using H-1 NMR and NOE methods, and the structure for polyheterocycle 45, obtained during attempted preparation of the sixth possible dioxopiperazine diastereomer 10, was determined with the additional aid of 2D COSY, 2D HETCOR, and H-1-C-13 correlation of long-range coupling (COLOC). Taken together, these studies provide evidence for the differences in reaction conditions required for bis(dioxopiperazine) synthesis, a relatively comprehensive analysis of dioxopiperazine and hydroxyl substituent effects on cyclohexane DMSO-d6 solution conformations, and a preliminary analysis of aqueous solubility differences.