2-(4-methoxybenzylidene)-1,3-propylene diacetate | 866129-27-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-methoxybenzylidene)-1,3-propylene diacetate
• 英文别名: [2-(Acetyloxymethyl)-3-(4-methoxyphenyl)prop-2-enyl] acetate
• CAS: 866129-27-3
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: DUGURZNYKJOKNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-methoxybenzylidene)-1,3-propylene diacetate 在 lipase PS-D (Pseudomonas cepacia, Amano) 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 30.0h， 生成 (E)-2-(hydroxymethyl)-3-(4-methoxyphenyl)prop-2-enyl acetate
  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：

  在 吡啶 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 9.0h， 生成 2-(4-methoxybenzylidene)-1,3-propylene diacetate
  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

• C(sp3)-C(sp3) Bond Breaking in Methylenecyclopropanes Involving a AuI/AuIII Catalytic Cycle
  作者：Di-Han Zhang、Lun-Zhi Dai、Min Shi

  DOI：10.1002/ejoc.201000765

  日期：——

  Gold(I) can catalyze the diacetoxylation of methylenecyclopropanes to produce the corresponding diacetoxylated products in moderate to good yields in acetic acid in the presence of iodosobenzene diacetate via C-C bond breaking under mild condition

  Gold(I) 可以在二乙酸碘苯酯的存在下，在温和条件下通过 CC 键断裂，催化亚甲基环丙烷的二乙酰氧基化反应，以中等至良好的产率在乙酸中生成相应的二乙酰氧基化产物
• Highly Regioselective Hydrolysis of Substituted 2-Benzylidene-1,3-propylene Diacetates Using Porcine Pancreas Lipase
  作者：Tsuyoshi Miura、Yuya Kawashima、Satoe Umetsu、Daisuke Kanamori、Nanae Tsuyama、Yuki Jyo、Yasuoki Murakami、Nobuyuki Imai

  DOI：10.1246/cl.2007.814

  日期：2007.6.5

  Hydrolysis of substituted 2-benzylidene-1,3-propylene diacetates in the presence of 100 w/w % of porcine pancreas lipase (PPL) Type II proceeded to afford the corresponding Z-monoacetates in excellent yields with high regioselectivities.

  在100% w/w的猪胰腺脂肪酶（PPL）Ⅱ的存在下，取代的2-苯基亚甲基-1,3-丙烯二乙酸酯的水解反应顺利进行，得到了相应的Z-单乙酸酯，产率极高，并具有良好的区域选择性。
• 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.
• US7705045B2
  申请人：——

  公开号：US7705045B2

  公开（公告）日：2010-04-27