2-(4-methoxybenzylidene)propane-1,3-diol | 866129-17-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: 2-(4-methoxybenzylidene)propane-1,3-diol
• 英文别名: 2-[(4-Methoxyphenyl)methylidene]propane-1,3-diol；2-[(4-methoxyphenyl)methylidene]propane-1,3-diol
• CAS: 866129-17-1
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: JBUCRCFLFPCLHL-UHFFFAOYSA-N

物化性质

• 熔点：
  69-70 °C
• 沸点：
  388.9±37.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-methoxybenzylidene)propane-1,3-diol 在 lipase PS-D (Pseudomonas cepacia, Amano) 吡啶 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 35.0h， 生成
  参考文献：
  名称：

  Highly regioselective lipase-catalyzed acetylation and hydrolysis of acyclic α,α′-alkenediols and their diacetates

  摘要：

  Highly regioselective transformation of acyclic alpha,alpha'-alkenediols and their corresponding diacetates to monoacetates using lipase was accomplished. The acetylation of the alpha,alpha'-alkenediol regioselectively gave (E)-monoacetate, whereas the (Z)-monoacetate were obtained by hydrolysis of the alpha,alpha'-diacetate. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.039
• 作为产物：
  描述：

  4-甲氧基苄基三苯基膦溴化盐 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 2-(4-methoxybenzylidene)propane-1,3-diol
  参考文献：
  名称：

  Highly regioselective lipase-catalyzed acetylation and hydrolysis of acyclic α,α′-alkenediols and their diacetates

  摘要：

  Highly regioselective transformation of acyclic alpha,alpha'-alkenediols and their corresponding diacetates to monoacetates using lipase was accomplished. The acetylation of the alpha,alpha'-alkenediol regioselectively gave (E)-monoacetate, whereas the (Z)-monoacetate were obtained by hydrolysis of the alpha,alpha'-diacetate. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.039

文献信息

• A Convenient Synthesis of the (<i>E</i>)-Monoacetates of 2-Alkylidenepropane-1,3-diols
  作者：Nobuyuki Imai、Tsuyoshi Miura、Kenjiro Okazaki、Kyoko Ogawa、Erika Otomo、Satoe Umetsu、Mauko Takahashi、Yuya Kawashima、Yuki Jyo、Naka Koyata、Yasuoki Murakami

  DOI：10.1055/s-2008-1067211

  日期：2008.9

  Various kinds of 3-substituted (E)-2-(hydroxymethyl)prop-2-enyl acetates were conveniently obtained in excellent yields by the regiospecific acetylation of 2-alkylidenepropane-1,3-diols with 10 equivalents of vinyl acetate in the presence of 50% w/w porcine pancreatic lipase (PPL) type II; the starting materials or (Z)-monoacetate or diacetate byproducts were generally not present.

  通过在50% w/w的猪胰脂肪酶（PPL）II型存在下，用10等摩尔的乙烯醋酸酯对2-烷基烯丙基-1,3-二醇进行区域特异性醋酸酯化，可以方便地获得各种3-取代的(E)-2-(羟甲基)丙-2-烯基醋酸酯，且收率极高；起始材料或(Z)-单醋酸酯或双醋酸酯副产物一般不存在。
• Regiospecific Acetylation of Substituted α,α′‐Benzylidenedimethanols with Vinyl Acetate using Porcine Pancreas Lipase
  作者：Tsuyoshi Miura、Yuya Kawashima、Mauko Takahashi、Yasuoki Murakami、Nobuyuki Imai

  DOI：10.1080/00397910701544760

  日期：2007.9.1
• Convenient synthesis of Z-monoacetates of 2-alkylidene-1,3-propanediols
  作者：Tsuyoshi Miura、Satoe Umetsu、Daisuke Kanamori、Nanae Tsuyama、Yuki Jyo、Yuya Kawashima、Naka Koyata、Yasuoki Murakami、Nobuyuki Imai

  DOI：10.1016/j.tet.2008.07.020

  日期：2008.9

  Various kinds of 3-substituted (Z)-hydroxymethyl-2-propenyl acetates were conveniently obtained in excellent yields by highly regioselective hydrolysis of 2-alkylidene-1,3-propylene diacetates in the presence of 100 w/w % of porcine pancreas lipase (PPL)Type II. (C) 2008 Elsevier Ltd. All rights reserved.
• Highly regioselective lipase-catalyzed acetylation and hydrolysis of acyclic α,α′-alkenediols and their diacetates
  作者：Takaya Hisano、Kotoko Onodera、Yasuhiro Toyabe、Nobuyuki Mase、Hidemi Yoda、Kunihiko Takabe

  DOI：10.1016/j.tetlet.2005.07.039

  日期：2005.9

  Highly regioselective transformation of acyclic alpha,alpha'-alkenediols and their corresponding diacetates to monoacetates using lipase was accomplished. The acetylation of the alpha,alpha'-alkenediol regioselectively gave (E)-monoacetate, whereas the (Z)-monoacetate were obtained by hydrolysis of the alpha,alpha'-diacetate. (c) 2005 Elsevier Ltd. All rights reserved.