methyl 4-{[(1E)-3-methoxy-3-oxo-1-propenyl]oxy}-2-hexynoate | 600678-32-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 4-{[(1E)-3-methoxy-3-oxo-1-propenyl]oxy}-2-hexynoate
• 英文别名: methyl 4-[(E)-3-methoxy-3-oxoprop-1-enoxy]hex-2-ynoate
• CAS: 600678-32-8
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: CSBDGYYCZOKWLO-BQYQJAHWSA-N

物化性质

• 沸点：
  338.0±27.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  methyl 4-{[(1E)-3-methoxy-3-oxo-1-propenyl]oxy}-2-hexynoate 在 lithium hydroxide 、 silica gel 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 1-Benzyl-5-carboxymethyl-4-ethyl-1H-pyrrole-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Antiproliferative activity in HL60 cells by tetrasubstituted pyrroles: a structure–activity relationship study

  摘要：

  A number of tetrasubstituted pyrrole derivatives have been synthesized and evaluated for their in vitro antiproliferative activities using the human promyelocytic leukemia cell line HL60. Tetrasubstituted pyrroles are obtained by irradiation of a silica gel absorbed mixture of a conjugated alkynoate and a primary amine. Active compounds exhibited GI(50) values in the range 445 mu M, and only six products showed TGI values within the evaluation range. A structure-activity relationship is also discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.069
• 作为产物：
  描述：

  丙醛 、 丙炔酸甲酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到methyl 4-{[(1E)-3-methoxy-3-oxo-1-propenyl]oxy}-2-hexynoate
  参考文献：
  名称：

  基于在醛或活性酮存在下催化生成非金属化共轭乙炔化物的高效多米诺工艺。

  摘要：

  据报道，非金属化的共轭乙炔化物极其温和高效地催化生成。这些乙炔化物通过连续的多键形成方法用于生成烯醇保护的官能化炔丙醇1、1,3-二氧戊环化合物2或3,4,5-三取代的4,5-二氢呋喃4。该方法要求使用亲核试剂（叔胺或膦）作为化学活化剂，使用共轭末端乙炔作为乙炔化物来源，并使用醛或活化酮作为亲电子试剂。该过程的化学结果取决于亲核试剂，温度，化学计量和溶剂的性质，它可以有选择地通过的实验条件的适当选择来定制。

  DOI：

  10.1002/chem.200204579

文献信息

• A Modular, One-Pot, Four-Component Synthesis of Polysubstituted 1,3-Oxazolidines
  作者：David Tejedor、Alicia Santos-Expósito、David González-Cruz、José Juan Marrero-Tellado、Fernando García-Tellado

  DOI：10.1021/jo048469q

  日期：2005.2.1

  A modular, one-pot, two-step, four-component synthesis of polysubstituted 1,3-oxzolidines is described. The method comprises two linked domino processes: an organocatalyzed domino reaction of alkyl propiolate and an aliphatic aldehydes and a microwave-assisted amine addition cyclization domino process. An alternative modular, one-pot, three-step, four-component synthesis has also been developed by

  描述了多取代的1，3-恶唑烷的模块化，一锅，两步，四组分合成。该方法包括两个连锁的多米诺方法：丙酸烷基酯和脂族醛的有机催化多米诺反应和微波辅助胺加成环化多米诺方法。通过将有机催化的多米诺法与顺序的胺加成/ Yb（OTf）3催化的烯胺环化反应联系起来，也开发了一种可替代的模块化，一锅，三步，四组分合成方法。
• A Diversity-Oriented Strategy for the Construction of Tetrasubstituted Pyrroles via Coupled Domino Processes
  作者：David Tejedor、David González-Cruz、Fernando García-Tellado、José Juan Marrero-Tellado、Matías López Rodríguez

  DOI：10.1021/ja047396p

  日期：2004.7.14

  A new microwave-assisted rearrangement of 1,3-oxazolidines scaffolds is the basis for a new, metal-free, direct, and modular construction of tetrasubstituted pyrroles from terminal-conjugated alkynes, aldehydes, and primary amines. This new reaction manifold entails two linked domino processes in a one-pot manner with both atom- and bond-efficiency and under very simple and environment-friendly experimental conditions.
• Efficient Domino Process Based on the Catalytic Generation of Non-Metalated, Conjugated Acetylides in the Presence of Aldehydes or Activated Ketones
  作者：David Tejedor、Fernando García-Tellado、José Juan Marrero-Tellado、Pedro de Armas

  DOI：10.1002/chem.200204579

  日期：2003.7.7

  acetylides are used to generate enol-protected functionalized propargylic alcohols 1, 1,3-dioxolane compounds 2, or 3,4,5-trisubstituted 4,5-dihydrofurans 4 through serial multibond-forming processes. The method calls for a nucleophile (a tertiary amine or phosphine) as a chemical activator, a conjugated terminal acetylene as the acetylide source, and an aldehyde or activated ketone as the electrophilic

  据报道，非金属化的共轭乙炔化物极其温和高效地催化生成。这些乙炔化物通过连续的多键形成方法用于生成烯醇保护的官能化炔丙醇1、1,3-二氧戊环化合物2或3,4,5-三取代的4,5-二氢呋喃4。该方法要求使用亲核试剂（叔胺或膦）作为化学活化剂，使用共轭末端乙炔作为乙炔化物来源，并使用醛或活化酮作为亲电子试剂。该过程的化学结果取决于亲核试剂，温度，化学计量和溶剂的性质，它可以有选择地通过的实验条件的适当选择来定制。
• Antiproliferative activity in HL60 cells by tetrasubstituted pyrroles: a structure–activity relationship study
  作者：José M. Padrón、David Tejedor、Alicia Santos-Expósito、Fernando García-Tellado、Víctor S. Martín、Jesús Villar

  DOI：10.1016/j.bmcl.2005.03.069

  日期：2005.5

  A number of tetrasubstituted pyrrole derivatives have been synthesized and evaluated for their in vitro antiproliferative activities using the human promyelocytic leukemia cell line HL60. Tetrasubstituted pyrroles are obtained by irradiation of a silica gel absorbed mixture of a conjugated alkynoate and a primary amine. Active compounds exhibited GI(50) values in the range 445 mu M, and only six products showed TGI values within the evaluation range. A structure-activity relationship is also discussed. (c) 2005 Elsevier Ltd. All rights reserved.