D-1-O-benzoyl-myo-inositol

• 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: D-1-O-benzoyl-myo-inositol
• 英文别名: (+/-)-1-O-benzoyl-myo-inositol；DL-1-O-benzoyl-myo-inositol
• 化学式: C₁₃H₁₆O₇
• 分子量: 284.266
• InChiKey: USFAYASKIQJDGW-KCUSNBPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.97
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  127.45
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  D-1-O-benzoyl-myo-inositol 在 双氧水 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Benzoic acid (1R,2S,3S,4R,5R,6S)-2,3,4,5,6-pentakis-(diethoxy-phosphoryloxy)-cyclohexyl ester
  参考文献：
  名称：

  Syntheses of two enantiomeric pairs of myo-inositol(1,2,4,5,6) and -(1,2,3,4,5) pentakisphosphate

  摘要：

  Two enantiomeric pairs of myo-inositol(1,2,4,5,6)P-5 and -(1,2,3,4,5)P-5 have efficiently been synthesized by means of the lipase catalyzed acetylation of 1,2:5,6-di-O-isopropylidene-myo-inositol and the benzoyl migration procedure. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00245-5
• 作为产物：
  描述：

  (±)-1,2:5,6-di-O-isopropylidene-myo-inositol 在 吡啶 、 溶剂黄146 作用下， 反应 1.0h， 生成 D-1-O-benzoyl-myo-inositol
  参考文献：
  名称：

  Syntheses of two enantiomeric pairs of myo-inositol(1,2,4,5,6) and -(1,2,3,4,5) pentakisphosphate

  摘要：

  Two enantiomeric pairs of myo-inositol(1,2,4,5,6)P-5 and -(1,2,3,4,5)P-5 have efficiently been synthesized by means of the lipase catalyzed acetylation of 1,2:5,6-di-O-isopropylidene-myo-inositol and the benzoyl migration procedure. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00245-5

文献信息

• Chiral desymmetrisation of myo-inositol 1,3,5-orthobenzoate gives rapid access to precursors for second messenger analogues
  作者：Andrew M. Riley、H. Yasmin Godage、Mary F. Mahon、Barry V.L. Potter

  DOI：10.1016/j.tetasy.2005.12.008

  日期：2006.1

  Chiral desymmetrisation of myo-inositol 1,3,5-orthobenzoate via the formation of diastereoisomeric bis[(1S)-(−)-camphanate] esters provides a convenient and fast route to precursors for biologically important inositol phosphates and lipids, and to synthetic analogues and probes modified at O-1 or O-3 of the inositol ring.

  的手性去对称肌肉经由非对映异构双[（1-形成肌醇1,3,5- orthobenzoate小号- （ - ） - ）莰烷]酯提供了前体的方便和快速的路径为生物学上重要的肌醇磷酸盐和脂质，并肌醇环的O-1或O-3修饰的合成类似物和探针。
• Regioselective hydrolysis of myo-inositol 1,3,5-orthobenzoate via a 1,2-bridged 2′-phenyl-1′,3′-dioxolan-2′-ylium ion provides a rapid route to the anticancer agent Ins(1,3,4,5,6)P₅
  作者：Himali Y. Godage、Andrew M. Riley、Timothy J. Woodman、Barry V. L. Potter

  DOI：10.1039/b605392k

  日期：——

  Acid hydrolysis of myo-inositol 1,3,5-orthobenzoate leads regioselectively to 2-O-benzoyl-myo-inositol via a 1,2-bridged 2′-phenyl-1′,3′-dioxolan-2′-ylium ion observed by 1H and 13C NMR spectroscopy, providing the precursor for a highly efficient route to the anticancer agent myo-inositol 1,3,4,5,6-pentakisphosphate.

  酸水解肌醇1,3,5-邻苯酯选择性地生成2-O-苯甲酰-肌醇，经过1,2-桥联的2ʹ-苯基-1ʹ,3ʹ-二氧烷-2ʹ-阳离子，这一过程通过1H和13C NMR谱得到观察，从而提供了一个高效合成抗癌剂肌醇1,3,4,5,6-五磷酸的前体。
• Regioselective Opening of <i>myo</i>-Inositol Orthoesters: Mechanism and Synthetic Utility
  作者：Himali Y. Godage、Andrew M. Riley、Timothy J. Woodman、Mark P. Thomas、Mary F. Mahon、Barry V. L. Potter

  DOI：10.1021/jo3027774

  日期：2013.3.15

  Acid hydrolysis of myo-inositol 1,3,5-orthoesters, apart from orthoformates, exclusively affords the corresponding 2-O-acyl myo-inositol products via a 1,2-bridged five-membered ring dioxolanylium ion intermediate observed by NMR spectroscopy. These C-2-substituted inositol derivatives provide valuable precursors for rapid and highly efficient routes to 2-O-acyl inositol 1,3,4,5,6-pentakisphosphates

  的酸水解肌醇肌醇1,3,5-原酸酯，除了原甲酸酯，只得到相应的2- ø -酰基肌醇经由1,2-桥连的五元环dioxolanylium离子中间体通过NMR光谱法观察到肌醇产品。这些C-2取代的肌醇衍生物2-提供快速和高效的路由有价值的前体ö酰基肌醇1,3,4,5,6- pentakisphosphates和肌肌醇1,3,4,5,6- pentakisphosphate具有生物学意义和抗癌特性。将氘掺入此类烷基酯产物 (2- O -C(O)CD 2 )的 α-亚甲基中R），当类似的原酸酯烷基用氘化的酸处理，在建立利用新颖的原酸酯肌肌醇1,3,5- orthobutyrate作为一个例子。这种氘代酯产品为氘标记的合成类似物提供了中间体。对 2- O-酯产物的这种选择性形成和氘掺入的研究与来自 NMR 实验的建议机制一起呈现。
• Regioselective functionalization of unprotected myo-inositol by electrophilic substitution
  作者：Yutaka Watanabe、Tsuyoshi Uemura、Satoe Yamauchi、Kousei Tomita、Takafumi Saeki、Ryousuke Ishida、Minoru Hayashi

  DOI：10.1016/j.tet.2013.03.109

  日期：2013.6

  Unprotected myo-inositol was treated with various electrophiles, such as aroyl chlorides, tosyl chloride and tert-butyldiphenylsilyl chloride in a solution of LiCl/DMA or DMSO to afford regioselectively l,3-di-O-substituted or racemic 1-O-substituted derivatives, depending on a quantity of reagents and reaction time. alpha-Unbranched alkanoic acid anhydrides in LiCl/DMA in the presence of triethylamine were suitable for acylation of myo-inositol, in contrast to the fact that acylation using alkanoyl chlorides in aprotic polar solvents generally does not proceed well due to decomposition of the reagents by the reaction with the solvents. (C) 2013 Elsevier Ltd. All rights reserved.