Benzenepropanoic acid, a-acetyl-2-iodo-, methyl ester | 926624-45-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzenepropanoic acid, a-acetyl-2-iodo-, methyl ester
• 英文别名: methyl 2-(2-iodobenzyl)-3-oxobutanoate；methyl 2-(2-iodobenzyl)-3-oxobutyrate
• CAS: 926624-45-5
• 化学式: C₁₂H₁₃IO₃
• 分子量: 332.138
• InChiKey: NPNGZNFCIVHLDS-UHFFFAOYSA-N

物化性质

• 沸点：
  363.9±27.0 °C(Predicted)
• 密度：
  1.571±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Benzenepropanoic acid, a-acetyl-2-iodo-, methyl ester 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 copper(l) iodide 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 27.0h， 生成
  参考文献：
  名称：

  级联反应：通过串联钯催化的氨基甲酰化/碳环化过程的功能化茚满衍生物的多组分方法

  摘要：

  AbstractA novel, multicomponent and stereoselective approach to functionalized indane derivatives is reported. It is based on a tandem process consisting of Pd‐catalyzed oxidative carbamoylation of 2‐(2‐ethynylbenzyl)malonates with carbon monoxide, a secondary amine, and oxygen (with formation of a propiolamide intermediate), followed by carbocyclization, occurring through intramolecular addition of an in situ formed carbanion to the propiolamide moiety.magnified image

  DOI：

  10.1002/adsc.201301051
• 作为产物：
  描述：

  2-碘苄醇 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 Benzenepropanoic acid, a-acetyl-2-iodo-, methyl ester
  参考文献：
  名称：

  Synthesis of Functionalized Alkylidene Indanes and Indanones through Tandem Phosphine–Palladium Catalysis

  摘要：

  Densely functionalized alkylidene indanes and indanones can be prepared efficiently in On pot, in high yields with good stereoselectivities (in some cases exclusively the Z-isomer), through a route involving phosphine-catalyzed Michael addition followed by palladium-catalyzed Heck cyclization. These transformations tolerate substrates bearing various substituents around the indane/indanone motif. Employing this technology, a concise formal synthesis of sulindac, nonsteroidal anti-inflammatory drug, has been established.

  DOI：

  10.1021/acs.orglett.5b00554

文献信息

• Highly Regio- and Stereoselective Synthesis of Indene Derivatives via Electrophilic Cyclization
  作者：Hai-Peng Bi、Li-Na Guo、Xin-Hua Duan、Fa-Rong Gou、Shu-Hao Huang、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1021/ol062683e

  日期：2007.2.1

  [reaction: see text] Indene or naphthalene derivatives are readily prepared in moderate to excellent yields with high regio- and stereoselectivity under very mild reaction conditions by the reaction of acetylenic malonates and ketones with I2, ICl, or NIS. The resulting iodides can be further elaborated using palladium-catalyzed coupling reactions.

  [反应：见正文]通过炔属丙二酸酯和酮与I2，IC1或NIS的反应，在非常温和的反应条件下，可以以中等至优异的收率和高的区域选择性和立体选择性轻松制备茚或萘衍生物。所得的碘化物可使用钯催化的偶联反应进一步精制。
• Palladium-catalyzed insertion of α,β-unsaturated N-tosylhydrazones and trapping with carbon nucleophiles
  作者：Yu-Ying Ye、Ping-Xin Zhou、Jian-Yi Luo、Mei-Jin Zhong、Yong-Min Liang

  DOI：10.1039/c3cc45583a

  日期：——

  Palladium-catalyzed carbene migratory insertion–cyclization reactions were reported, delivering dihydronaphthalene and indene derivatives in moderate to good yields. A three-component cross-coupling was also developed. The reactions are easy to handle, under mild conditions and various functional groups are tolerated.

  报告了钯催化的碳烯迁移插入环化反应，以中等至良好的产率获得了二氢萘和茚衍生物。此外，还开发了一种三组分交叉偶联反应。这些反应易于处理，条件温和，可容忍各种官能团。
• Cyclization of Nonterminal Alkynic β-Keto Esters Catalyzed by Gold(I) Complex with a Semihollow, End-Capped Triethynylphosphine Ligand
  作者：Hideto Ito、Yusuke Makida、Atsuko Ochida、Hirohisa Ohmiya、Masaya Sawamura

  DOI：10.1021/ol802079r

  日期：2008.11.6

  A cationic gold(l) complex with a semihollow-shaped trialkynylphosphine catalyzed 5-exo-dig and 6-endo-dig cyclizations of various internal alkynic beta-keto esters, showing a marked advantage over a gold(I)-PPh3 complex with respect to the rates of the reactions and the product yields. It is proposed that the gold-bound alkynic substrate in a catalytic pocket must be somewhat folded and that such a steric effect makes the carbon-carbon bond formation entropically more favorable.