(1S,2R,3R,4R)-3,4-O-Isopropylidenecyclohex-5-ene-1,2,3,4-tetraol | 139013-60-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,3R,4R)-3,4-O-Isopropylidenecyclohex-5-ene-1,2,3,4-tetraol
• 英文别名: (3aS,4R,5S,7aR)-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxole-4,5-diol
• CAS: 139013-60-8
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: VCIXQRISGLSULF-LXGUWJNJSA-N

物化性质

• 沸点：
  313.5±42.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R,3R,4R)-3,4-O-Isopropylidenecyclohex-5-ene-1,2,3,4-tetraol 在 Amberlyst A-27 、 水 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 muco-inositol
  参考文献：
  名称：

  Inositol synthesis: concise preparation of l-chiro-inositol and muco-inositol from a common intermediate

  摘要：

  Fully stereoselective large-scale syntheses have been attained for L-chiro-inositol (2) and muco-inositol (3) by means of controlled peripheral oxygenation of cyclohexadiene diol 1. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00182-7
• 作为产物：
  描述：

  [3aS-(3aα,5aβ,6aβ,6bα)]-4-溴-3a,5a,6a,6b-四氢-2,2-二甲基环氧乙烷并[e]-1,3-苯并二茂 在 氢氧化钾 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 生成 (1S,2R,3R,4R)-3,4-O-Isopropylidenecyclohex-5-ene-1,2,3,4-tetraol
  参考文献：
  名称：

  Inositol synthesis: concise preparation of l-chiro-inositol and muco-inositol from a common intermediate

  摘要：

  Fully stereoselective large-scale syntheses have been attained for L-chiro-inositol (2) and muco-inositol (3) by means of controlled peripheral oxygenation of cyclohexadiene diol 1. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00182-7

文献信息

• Selective electrochemical deprotection of cinnamyl ethers, esters, and carbamates
  作者：Jeff Hansen、Stanley Freeman、Tomas Hudlicky

  DOI：10.1016/s0040-4039(03)00009-1

  日期：2003.2

  Electrochemical deprotection of the cinnamyl moiety from ethers, esters, and carbamates was studied with the focus on O- versus N- selectivity as well as selectivity over allyl or benzyl systems.

  研究了肉桂基部分与醚，酯和氨基甲酸酯的电化学脱保护作用，重点是O-对N-选择性以及对烯丙基或苄基系统的选择性。
• Use of Electrochemical Methods as an Alternative to Tin Reagents for the Reduction of Vinyl Halides in Inositol Synthons
  作者：Tomas Hudlicky、Christopher D. Claeboe、Larry E. Brammer、Lukasz Koroniak、Gabor Butora、Ion Ghiviriga

  DOI：10.1021/jo990382v

  日期：1999.6.1

  previously used in inositol syntheses were subjected to electrochemical reduction. The unreactivity of allylic alcohols or allylic ethers at the applied potentials allowed the selective reduction of vinyl halides to olefins. Electrochemical methods provide for selective reduction of vinyl iodides over vinyl bromides, with better yields than analogous tin methodology. Cinnamyl ethers were reductively

  将先前用于肌醇合成的几种乙烯基卤化物进行电化学还原。烯丙基醇或烯丙基醚在所施加的电势下的不反应性使得卤化乙烯选择性地还原为烯烃。电化学方法提供了比乙烯基溴选择性还原乙烯基碘的方法，其收率高于类似的锡方法。在烷基烯丙基醚存在下，肉桂醚在-3.2 V（vs Ag / AgNO（3））上进行还原裂解，以提供选择性脱保护。在乙烯基环氧乙烷或乙烯基氮丙啶的存在下，卤化乙烯的电化学还原伴随着应变环的溶剂分解。报告了产率和条件，并将其与标准锡诱导的脱卤方法进行了比较。
• Selective electrochemical reduction of cinnamyl ethers in the presence of other allylic C O bonds
  作者：Aida Solis-Oba、Tomas Hudlicky、Lukasz Koroniak、Dean Frey

  DOI：10.1016/s0040-4039(00)02250-4

  日期：2001.2

  Several conduritol derivatives protected as allyl and cinnamyl ethers were subjected to electrochemical reduction at a mercury cathode, resulting in selective removal of the cinnamyl group.

  将几种被保护为烯丙基和肉桂基醚的conduritol衍生物在汞阴极上进行电化学还原，从而选择性除去了肉桂基。
• Chemoselective Nozaki–Hiyama–Takai–Kishi and Grignard reaction: short synthesis of some carbahexopyranoses
  作者：Allam Vinaykumar、Banothu Surender、Batchu Venkateswara Rao

  DOI：10.1039/d3ra03704e

  日期：——

  efficient, stereoselective and short approach for the total syntheses of some carbahexopyranoses namely, MK7607, (−)-gabosine A, (−)-conduritol E, (−)-conduritol F, 6a-carba-β-D-fructopyranose and other carbasugars using chemoselective Grignard or Nozaki–Hiyama–Takai–Kishi (NHTK) reactions and RCM. Herein, the Grignard and NHTK reactions are able to differentiate the reactivity difference between lactol

  一种通用、发散、高效、立体选择性和简短的方法，用于全合成某些吡喃碳糖，即 MK7607、(−)-gabosine A、(−)-conduritol E、(−)-conduritol F、6a-carba-β- D -吡喃果糖和其他卡巴糖，使用化学选择性格氏反应或野崎-桧山-高井-岸 (NHTK) 反应和 RCM。在此，格氏反应和NHTK反应能够在给定条件下区分乳醇或乳醇乙酸酯与醛2和6之间的反应性差异，以给出所需的骨架化学选择性。
• Hudlicky, Tomas; Luna, Hector; Olivo, Horacio F., Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 2907 - 2918
  作者：Hudlicky, Tomas、Luna, Hector、Olivo, Horacio F.、Andersen, Catherine、Nugent, Thomas、Price, John D.

  DOI：——

  日期：——