1,3-diiodo-2-(iodomethyl)propane | 66587-78-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1,3-diiodo-2-(iodomethyl)propane
• 英文别名: 1,3-diiodo-2-iodomethyl-propane；2-iodomethyl-1,3-diiodopropane
• CAS: 66587-78-8
• 化学式: C₄H₇I₃
• 分子量: 435.813
• InChiKey: WZMJXLPRINPVGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,3-diiodo-2-(iodomethyl)propane 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 反应 16.0h， 以64%的产率得到3-碘-2-碘甲基丙烯
  参考文献：
  名称：

  Latour, Stephan; Wuest, James D., Synthesis, 1987, # 8, p. 742 - 744

  摘要：

  DOI：
• 作为产物：
  描述：

  1-bromo-3-chloro-2-chloromethyl-propane 在 sodium iodide 作用下， 以 丙酮 为溶剂， 生成 1,3-diiodo-2-(iodomethyl)propane
  参考文献：
  名称：

  Free-Radical Reactions of Diazomethane with Reactive Bromopolychloroalkanes

  摘要：

  DOI：

  10.1021/ja01063a032

文献信息

• WO2007/94680
  申请人：——

  公开号：——

  公开（公告）日：——
• Substrate-Controlled Group-Selective Radical Cyclizations. A New Strategy for Stereocontrolled Transformations of Diastereomeric Reactive Intermediates
  作者：Dennis P. Curran、Hongyan Qi、Nicholas C. DeMello、Chien-Hsing Lin

  DOI：10.1021/ja00097a086

  日期：1994.9
• Stereoselection at the Steady State. Group Selective Radical Cyclizations of Substrates Containing Two Radical Precursors and One Radical Acceptor
  作者：Dennis P. Curran、Chien-Hsing Lin、Nicholas DeMello、Jörg Junggebauer

  DOI：10.1021/ja9724102

  日期：1998.1.1

  The kinetic model for compound stereoselection presented in previous paper is verified experimentally by conducting a series of radical cyclizations of 1-(3-halo-2-(halomethyl)propyl)cycloalk-2-enecarboxylates with tributyltin hydride and measuring the ratios of products. Cyclization rate constants are abstracted from the data by an analysis that minimizes total error, and these rate constants compare favorably with rate constants that we measured directly on the corresponding monohalides. Transition state modeling was used to interpret the initial round of results and to design two new systems, one of which was predicted to cyclize with higher selectivity than the parent and the other of which was predicted to cyclize with reverse selectivity. These substrates bearing 4-tert-butyl groups were synthesized, and the experimental results verified the computational predictions.
• Attempted synthesis of 1,3,5-triphenyl-2,4,9-trithia-1,3,5-triplumbaadamantane. Decomposition of organolead iodides
  作者：Michio Kobayashi、Stephan Latour、James D. Wuest

  DOI：10.1021/om00054a069

  日期：1991.8

  MNDO calculations suggest that the strength of the bridgehead carbon-hydrogen bond in 2,4,9-trithia-1,3,5-triplumbaadamantane (2a) should be only 54 kcal/mol and the hydride affinity of the corresponding bridgehead cation 2a+ should be only 215 kcal/mol. As a donor of hydrogen atoms or hydride, plumbaadamantane 2a should therefore be even more reactive than the analogous stannaadamantane 1a. Unfortunately, substituted derivative 2b could not be prepared from (Ph3PbCH2)3CH by controlled iodinolysis followed by treatment of the intermediate hexaiodide (PhI2PbCH2)3CH with Ph3SnSSnPh3. This failure results in part from the tendency of organolead diiodides R2PbI2 to undergo redistribution reactions that produce unstable triiodides RPbI3. Diiodides capable of intramolecular redistributions are particularly reactive. The resulting triiodides then decompose by a formal reductive elimination of RI and PbI2. Since the iodinolysis of (cyclopropylmethyl)triphenylplumbane (11) yields mainly (iodomethyl)cyclopropane instead of ring-opened products derived from cyclopropylmethyl cations or radicals, we suggest that the reductive elimination of RI and PbI2 from RPbI3 is concerted.
• LATOUR, S.;WUEST, J. D., SYNTHESIS,(1987) N 8, 742-745
  作者：LATOUR, S.、WUEST, J. D.

  DOI：——

  日期：——