3-phenyl-1,3,3-trideuterio-1-propyne | 10147-10-1

• 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: 3-phenyl-1,3,3-trideuterio-1-propyne
• 英文别名: 1-phenyl-[1,1,3-(2)H3]-2-propyne；3-Phenyl-1,3,3-trideuterio-propin；3-Phenylpropin-1,3,3-d(3)；1,1,3-trideuterioprop-2-ynylbenzene
• CAS: 10147-10-1
• 化学式: C₉H₈
• 分子量: 119.139
• InChiKey: NGKSKVYWPINGLI-YOWJZXODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  9.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  3-phenyl-1,3,3-trideuterio-1-propyne 、 碘甲烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 生成 1-phenyl-[1,1-2H3]-2-butyne
  参考文献：
  名称：

  [（RCN）2PdCl2]-烯烃的E / Z异构化：非氢化物双核加成-消除途径

  摘要：

  曙光催化剂：[[RCN）2 PdCl 2 ]配合物催化的烯烃迁移通过原位生成的Pd-H物质进行。1,5-二烯的添加抑制迁移，并允许研究较慢的E / Z互转换背景催化。实验和计算结果表明，这种相互转化是通过二丙环中的构象平衡进行的（参见图片）。

  DOI：

  10.1002/anie.201103947
• 作为产物：
  描述：

  1-苯基-1-丙炔 在 正丁基锂 、 重水 作用下， 生成 3-phenyl-1,3,3-trideuterio-1-propyne
  参考文献：
  名称：

  Acylpalladation of Internal Alkynes and Palladium-Catalyzed Carbonylation of (Z)-.beta.-Iodoenones and Related Derivatives Producing .gamma.-Lactones and .gamma.-Lactams

  摘要：

  The reaction of either an internal alkyne-organic halide mixture or (Z)-beta-iodoenones with CO in the presence of a Pd-phosphine catalyst, e.g., Cl2Pd(PPh(3))2, can give one of the three discrete types of compounds as the major products depending on the substrate structure and the reaction conditions. Those substrates which are convertible to (Z)-gamma-oxo-alpha,beta-unsaturated acylpalladium derivatives lacking delta-H atoms are converted to the corresponding 2-butenolides (13) in the presence of water, which serves as a H donor. Carbon monoxide most likely is the source of two electrons. Either in the absence of water (or any other suitable H source) or in the presence of some factors disfavoring the butenolide formation, the same reaction gives the corresponding dimeric product (16). Even in cases where there is an alpha-H atom in the alpha-substitutent, 1,4-elimination products (11), reported to be the major products in a related Pd-catalyzed reaction of terminal alkyne-aryl iodide mixtures with CO, were not detected. In sharp contrast, those substrates which can give rise to (Z)-gamma-oxo-alpha, beta-unsaturated acylpalladium derivatives containing delta-H atoms give, under comparable reaction conditions, enol lactones (12), i.e., (Z)-3-alkylidene-2-butenolides, contaminated with only very minor amounts of 22 even in cases where an excess (4 equiv) of water was present. The required (Z)-beta-iodoenones can be readily prepared in one pot via ZrCp(2)-promoted cyclization of alkynes with nitriles. The ready availability of the starting compounds and the high Z stereoselectivity make the overall sequence an attractive synthetic route to 12. The courses of the Pd-catalyzed carbonylation reactions of (Z)-beta-iodo-alpha,beta-unsaturated imines 23 closely parallel the reactions of enones and produce the corresponding lactams, i.e., 24 and 25.

  DOI：

  10.1021/ja00117a011

文献信息

• Maercker, Adalbert; Girreser, Ulrich, Angewandte Chemie, 1990, vol. 102, # 6, p. 718 - 720
  作者：Maercker, Adalbert、Girreser, Ulrich

  DOI：——

  日期：——