3-hydroxy-3-(3,4-methylenedioxyphenyl)propanenitrile | 51241-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3-hydroxy-3-(3,4-methylenedioxyphenyl)propanenitrile
• 英文别名: β-Hydroxy-β-<3,4-(methylenedioxy)phenyl>propionitrile；β-hydroxy-1,3-benzodioxole-5-propanenitrile；3-(Benzo[d][1,3]dioxol-5-yl)-3-hydroxypropanenitrile；3-(1,3-benzodioxol-5-yl)-3-hydroxypropanenitrile
• CAS: 51241-26-0
• 化学式: C₁₀H₉NO₃
• 分子量: 191.186
• InChiKey: WRFRLUPCPUPBKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  62.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hydroxy-3-(3,4-methylenedioxyphenyl)propanenitrile 在 aluminum (III) chloride 、 三氟甲磺酸三甲基硅酯 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 16.08h， 生成 2-(benzo[d][1,3]dioxol-5-yl)-6-methyltetrahydropyran-4-one
  参考文献：
  名称：

  β-羟基烯丙基酮的非对映选择性分子内环化反应合成顺-2,6-四氢吡喃-4-酮

  摘要：

  在Me 3 SiOTf为催化剂存在下，由β-羟基烯丙基酮的分子内环化反应合成了一系列顺式-2,6-四氢吡喃-4-酮。在Barbier型反应条件下，通过与β-羟基腈的烯丙基化反应制备β-羟基烯丙基酮，而没有保护羟基官能团。

  DOI：

  10.1016/j.tet.2012.02.076
• 作为产物：
  描述：

  胡椒醛 、 三甲基硅烷氰化甲烷 在 2,8,9-三异丙基-2,5,8,9-四硫唑嘌呤-1-磷杂二环[3.3.3]十一烷 、 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以82%的产率得到3-hydroxy-3-(3,4-methylenedioxyphenyl)propanenitrile
  参考文献：
  名称：

  P(i-PrNCH₂CH₂)₃N as a Lewis Base Catalyst for the Synthesis of β-Hydroxynitriles Using TMSAN

  摘要：

  Proazaphosphatrane 1a was found to be an efficient catalyst for synthesis of beta-hydroxynitriles via the reaction of trimethylsilylacetonitrile (TMSAN) with aldehydes under mild reaction conditions and typically low catalyst loading (ca. 2 mol%). A variety of functional groups were tolerated, and good to excellent product yields were obtained.

  DOI：

  10.1021/jo900814t

文献信息

• Synthetic applications of elementoorganic compounds of group 15 and 16. 85. Pentaalkyl stiboranes. 1. Synthesis of homobenzylic alcohols, homoallylic alcohols, homoallylic alcohols, ethyl 5-aryl-5-hydroxy-2-pentenoates, and .beta.-hydroxypropionic acid derivatives via pentaalkylstiboranes
  作者：Yaozeng Huang、Yi Liao

  DOI：10.1021/jo00004a010

  日期：1991.2

  Although pentaalkylstiboranes have long been known, their applications in organic synthesis have not been exploited. It has been found that quaternary stibonium salts (n-Bu3SbCH2E]+X- (E = Ph, CH = CH2, CH = CHCO2Et, CO2Et, CN; X = Br, I, BPh4) on treatment with RLi (R = n-Bu, t-Bu, Ph) afford pentaalkylstiboranes, n-Bu3Sb(R)CH2E, which react with aromatic aldehydes to give, after subsequent hydrolysis, homobenzylic alcohols, homoallylic alcohols, ethyl 5-aryl-5-hydroxypent-2-enoates, ethyl beta-aryl-beta-hydroxypropionates, and beta-aryl-beta-hydroxypropionitriles, respectively, in good to excellent yields. The reaction is chemoselective for aldehydes.
• Zhou, Zhang-Lin; Shi, Lin-Lan; Huang, Yao-Zeng, Journal of the Chemical Society. Perkin transactions I, 1991, # 8, p. 1931 - 1933
  作者：Zhou, Zhang-Lin、Shi, Lin-Lan、Huang, Yao-Zeng

  DOI：——

  日期：——
• P(<i>i</i>-PrNCH₂CH₂)₃N as a Lewis Base Catalyst for the Synthesis of β-Hydroxynitriles Using TMSAN
  作者：Kuldeep Wadhwa、John G. Verkade

  DOI：10.1021/jo900814t

  日期：2009.8.7

  Proazaphosphatrane 1a was found to be an efficient catalyst for synthesis of beta-hydroxynitriles via the reaction of trimethylsilylacetonitrile (TMSAN) with aldehydes under mild reaction conditions and typically low catalyst loading (ca. 2 mol%). A variety of functional groups were tolerated, and good to excellent product yields were obtained.
• Synthesis of cis-2,6-tetrahydropyran-4-one via diastereoselectively intramolecular cyclization of β-hydroxy allyl ketone
  作者：Adam Shih-Yuan Lee、Li-Shin Lin、Yu-Ting Chang

  DOI：10.1016/j.tet.2012.02.076

  日期：2012.5

  A series of cis-2,6-tetrahydropyran-4-ones was synthesized from the intramolecular cyclization reaction of β-hydroxy allyl ketones in the presence of Me3SiOTf as catalyst. The β-hydroxy allyl ketone was prepared from allylation reaction with β-hydroxynitrile without protection of hydroxy functionality under the Barbier-type reaction condition.

  在Me 3 SiOTf为催化剂存在下，由β-羟基烯丙基酮的分子内环化反应合成了一系列顺式-2,6-四氢吡喃-4-酮。在Barbier型反应条件下，通过与β-羟基腈的烯丙基化反应制备β-羟基烯丙基酮，而没有保护羟基官能团。