2-环亚丙基乙酸 | 5687-73-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-环亚丙基乙酸
• 英文名称: 2-cyclopropylideneacetic acid
• 英文别名: Cyclopropylideneacetic acid
• CAS: 5687-73-0
• 化学式: C₅H₆O₂
• mdl: MFCD09032653
• 分子量: 98.1014
• InChiKey: BUTJLJIPWQEYOC-UHFFFAOYSA-N

物化性质

• 熔点：
  62-63 °C
• 沸点：
  243.2±9.0 °C(Predicted)
• 密度：
  1.507±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2916209090

反应信息

• 作为反应物：
  描述：

  2-环亚丙基乙酸 在 copper(l) iodide 、 碘 作用下， 以 水 、 乙腈 为溶剂， 反应 10.0h， 以51%的产率得到4-碘-2,3-二氢吡喃-6-酮
  参考文献：
  名称：

  Facile and Effective Copper-Mediated Cyclization Reaction of Cyclopropylideneacetic Acids (or Esters) and Cyclopropylideneacetonitriles

  摘要：

  The full details of the copper-mediated cyclization reaction of cyclopropylideneacetic acids (or esters) and cyclopropylidenenitriles, the synthetic application of this reaction, and the study of the reaction mechanism are reported.

  DOI：

  10.1021/jo035225h
• 作为产物：
  描述：

  环亚丙基乙酸乙酯 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以72%的产率得到2-环亚丙基乙酸
  参考文献：
  名称：

  Diastereoselective Diels−Alder Reactions of a Novel Cyclopropenyl-Containing Chiral Auxiliary

  摘要：

  A novel cyclopropenyl-containing 1,3-spiroaminoalcohol auxiliary has been used in a variety of asymmetric Diels-Alder reactions providing endo adducts with diastereomeric ratios ranging from 2:1 up to >99:1. In addition, unexpected regiochemistry was observed for a Diels-Alder reaction between cyclopropenyl dienophile and 4-vinyl-1,2-dihydronapthalene.

  DOI：

  10.1021/ol702280q

文献信息

• Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of 1,6-Enynes with Cyclopropylideneacetamides
  作者：Soichi Yoshizaki、Yu Nakamura、Koji Masutomi、Tomoka Yoshida、Keiichi Noguchi、Yu Shibata、Ken Tanaka

  DOI：10.1021/acs.orglett.5b03387

  日期：2016.2.5

  It has been established that a cationic rhodium(I)/H8–BINAP complex catalyzes the asymmetric [2 + 2 + 2] cycloaddition of 1,6-enynes with cyclopropylideneacetamides to produce spirocyclohexenes in excellent enantioselectivity with retaining cyclopropane rings.

  现已确定，阳离子铑（I）/ H 8 -BINAP配合物可催化1，6-炔烃与环亚丙基乙酰胺的不对称[2 + 2 + 2]环加成反应，生成具有优异对映选择性并保留环丙烷环的螺环己烯。
• [4 + 2] Cycloaddition of thiophene S-monoxides to activated methylenecyclopropanes
  作者：Thies Thiemann、Daisuke Ohira、Yuanqiang Li、Tsuyoshi Sawada、Shuntaro Mataka、Karsten Rauch、Mathias Noltemeyer、Armin de Meijere

  DOI：10.1039/b003850o

  日期：——

  determined as being endo,syn. The Wittig olefination of cyclopropanone hemiacetal to generate the methylenecyclopropanes and the subsequent cycloaddition can be carried out in a one-pot operation. This procedure is one of many potential one-pot or multi-component reactions involving stabilized phosphoranes. A further example of this type of reaction is shown in the novel desilylation–Wittig olefination

  噻吩小号-oxides 4已经显示出经历[4 + 2]环加成与亚甲基环2与一个或两个电子受体取代基，即甚至在四取代的2-氯-2- cyclopropylideneacetate 2C反应很好。但是，对于四取代的烯烃双（亚环丙基）2f，必须施加高压使其与4反应。在所有反应中仅形成一种非对映异构体。的两个cycloadducts，X射线晶体结构分析图3a和3f中，已经执行，它们的相对配置确定为内切，顺。环丙烷半缩醛的Wittig烯烃化反应生成亚甲基环丙烷，随后的环加成反应可以一锅操作进行。该过程是涉及稳定的膦烷的许多潜在的一锅法或多组分反应之一。这种新型反应的另一个例子是新型的甲硅烷基化-1-乙氧基-1-三甲基甲硅烷基氧基环丙烷5的Wittig烯化反应，一步一步产生环亚丙基乙酸酯，例如2a。
• Rhodium-Catalyzed [3+2+2] and [2+2+2] Cycloadditions of Two Alkynes with Cyclopropylideneacetamides
  作者：Tomoka Yoshida、Yuki Tajima、Masayuki Kobayashi、Koji Masutomi、Keiichi Noguchi、Ken Tanaka

  DOI：10.1002/anie.201502505

  日期：2015.7.6

  It has been established that a cationic rhodium(I)/H8‐binap complex catalyzes the [3+2+2] cycloaddition of 1,6‐diynes with cyclopropylideneacetamides to produce cycloheptadiene derivatives through cleavage of cyclopropane rings. In contrast, a cationic rhodium(I)/(S)‐binap complex catalyzes the enantioselective [2+2+2] cycloaddition of terminal alkynes, acetylenedicarboxylates, and cyclopropylideneacetamides

  现已确定，阳离子铑（I）/ H 8 -binap配合物可催化1，6-二炔与环丙基亚乙乙酰胺的[3 + 2 + 2]环加成反应，通过环丙烷环的裂解产生环庚二烯衍生物。相反，阳离子铑（I）/（S）-双键合络合物催化末端炔烃，乙炔二羧酸酯和环亚丙基乙酰胺的对映选择性[2 + 2 + 2]环加成反应，生成保留环丙烷环的螺-环己二烯衍生物。
• Asymmetric Diels−Alder Reactions of Chiral Cyclopropylidene Imide Dienophiles:  Preparation of <i>gem</i>-Dimethyl- and Spirocyclopropane Norbornyl Carboxylic Acids
  作者：Jeffrey T. Kuethe、Dalian Zhao、Guy R. Humphrey、Michel Journet、Arlene E. McKeown

  DOI：10.1021/jo052516c

  日期：2006.3.1

  A highly efficient strategy has been developed for the rapid asymmetric synthesis of gem-dimethyl and spirocyclopropyl norbornyl carboxylic acids. The key transformation involved the unprecedented asymmetric Diels−Alder reaction of highly reactive β,β-cyclopropyl-α,β-unstaturated N-acyloxazolidinones with cyclopentadiene affording the adducts in high yield and de.

  已经开发了用于宝石-二甲基和螺环丙基降冰片基羧酸的快速不对称合成的高效策略。关键的转变涉及高反应性的β，β-环丙基-α，β-不饱和N-酰基恶唑烷酮与环戊二烯的空前的不对称Diels-Alder反应，从而以高收率和高收率提供加合物。
• Chromanol derivatives—A novel class of CETP inhibitors
  作者：Alexandros Vakalopoulos、Carsten Schmeck、Michael Thutewohl、Volkhart Li、Hilmar Bischoff、Klemens Lustig、Olaf Weber、Holger Paulsen、Harry Elias

  DOI：10.1016/j.bmcl.2010.10.110

  日期：2011.1

  Based on our former development candidate BAY 38-1315, optimization efforts led to the discovery of a novel chemical class of orally active cholesteryl ester transfer protein (CETP) inhibitors. The chromanol derivative 19b is a highly potent CETP inhibitor with favorable pharmacokinetic properties suitable for clinical studies. Chemical process optimization furnished a robust synthesis for a kilogram-scale process. (C) 2010 Elsevier Ltd. All rights reserved.