(S)-4-acetoxy-methyl-dihydrofuran-2-one | 133644-77-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (S)-4-acetoxy-methyl-dihydrofuran-2-one
• 英文别名: [(3S)-5-oxooxolan-3-yl]methyl acetate
• CAS: 133644-77-6
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: GDDJOYKPVHIRLU-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3S,Rs)-<3,4-dihydro-6-(p-tolylsulfinyl)methyl-2H-pyran-3-yl>methyl p-toluenesulfonate 在 sodium chlorite 、 sodium dihydrogenphosphate 、 二甲基硫 、 镍 、 臭氧 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 26.08h， 生成 (S)-4-acetoxy-methyl-dihydrofuran-2-one
  参考文献：
  名称：

  Asymmetric Desymmetrization of Prochiral 1,3-Diols via Diastereoselective C-O Bond Fission of Bicyclic Acetal Using a Chiral Sulfoxide as a Chiral Auxiliary.

  摘要：

  通过手性α-亚磺酰基缩醛6的不对称解对称化作用，实现了对映选择性的C-O键断裂，进而实现了对非手性1,3-二醇的对称性破缺。将6与四氯化钛反应主要得到经氧鎓离子中间体生成的7a，而与二异丙基氨锂反应则通过对映选择性的β-消除反应后进行烯烃异构化，选择性地获得了7b。

  DOI：

  10.1248/cpb.44.1146

文献信息

• Asymmetric functionalisation of prochiral 1,3-diols based on an efficient 1,6-chiral induction: the diastereoselective C–O bond fission in chiral β-arylsulfinyl acetal via two types of chelation control
  作者：Chuzo Iwata、Naoyoshi Maezaki、Manabu Murakami、Motohiro Soejima、Tetsuaki Tanaka、Takeshi Imanishi

  DOI：10.1039/c39920000516

  日期：——

  The novel asymmetric functionalisation of a prochiral 1,3-diol is accomplished by the diastereoselective C–O bond fission of the chiral β-arylsulfinyl acetal via two types of chelation controlled transition states (A and C in Scheme 4).

  前手性1,3-二醇的新型不对称官能化是通过手性β-芳基亚磺酰基缩醛的非对映选择性C-O键裂变，通过两种螯合控制的过渡态（方案4中的A和C）完成的。
• Mori, Kenji; Chiba, Naoki, Liebigs Annalen der Chemie, 1989, p. 957 - 962
  作者：Mori, Kenji、Chiba, Naoki

  DOI：——

  日期：——
• Asymmetric synthesis of a key synthetic precursor for(+)-strigol and sorgolactone
  作者：Josef Schröer、Peter Welzel

  DOI：10.1016/s0040-4020(01)81337-5

  日期：1994.1

  En-route to non-racemic iodomethyl butyrolactone 23g a number of stereoselective 1,4-additions and reductions have been studied. The only satisfactory approach involved baker's yeast reduction (21c-->23c) as key step.
• Chemoenzymatic synthesis of asymmetrized bis(hydroxymethyl)propanoates (BHYMP∗) as a new family of chiral building blocks
  作者：Luca Banfi、Andrea Basso、Giuseppe Guanti、Maria Teresa Zannetti

  DOI：10.1016/s0957-4166(97)00560-0

  日期：1997.12

  A series of asymmetrized bis(hydroxymethyl)propanoates (BHYMP*) has been prepared in both enantiomeric forms through a chemoenzymatic methodology involving complementary diacetate monohydrolyses and diol monoacetylations catalyzed by lipases. (C) 1997 Elsevier Science Ltd. All rights reserved.
• Asymmetric reduction of 3-hydroxymethylbutenolide derivatives by bakers' yeast: A new approach to the synthesis of factor-I
  作者：Kunihiko Takabe、Masaya Tanaka、Masahisa Sugimoto、Takashi Yamada、Hidemi Yoda

  DOI：10.1016/0957-4166(92)80012-l

  日期：1992.11

  Bakers' yeast reduction of 3-benzyloxymethylbutenolide gave (S)-3-benzyloxymethylbutanolide, and its transformation to Factor-I, the autoregulator of Streptomyces viridocchromogenes, was examined.