1,1-diiodo-2,2-dimethoxyethyl-2-phenylethanone | 74966-71-5

• 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: 1,1-diiodo-2,2-dimethoxyethyl-2-phenylethanone
• 英文别名: 1,1-Diiodo-2,2-dimethoxy-2-phenylethane；(2,2-Diiodo-1,1-dimethoxyethyl)benzene
• CAS: 74966-71-5
• 化学式: C₁₀H₁₂I₂O₂
• 分子量: 418.013
• InChiKey: LRZOAPVOZRNSRW-UHFFFAOYSA-N

物化性质

• 熔点：
  84-86 °C (decomp)
• 沸点：
  305.5±42.0 °C(Predicted)
• 密度：
  2.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1-diiodo-2,2-dimethoxyethyl-2-phenylethanone 反应 12.0h， 生成 2-碘-1-苯基乙酮 、 2,2-二碘-1-苯基乙烷-1-酮
  参考文献：
  名称：

  Iron(III) catalyzed halo-functionalization of alkynes

  摘要：

  Aromatic and aliphatic alkynes can be halo-functionalized to alpha,alpha-dihalodimethyl ketals catalyzed by FeCl3 in excellent yields. MeOH is used as a nucleophilic solvent and N-halosuccinimide as the halogen source for this efficient transformation. The resulting alpha,alpha-dibromodimethyl ketals can be converted to the corresponding alpha,alpha-dibromoketones by treatment with 8% FeCl3 in silica gel. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.05.039
• 作为产物：
  描述：

  甲醇 、 苯乙炔 在 iron(III) chloride 、 N-碘代丁二酰亚胺 作用下， 反应 5.0h， 以93%的产率得到1,1-diiodo-2,2-dimethoxyethyl-2-phenylethanone
  参考文献：
  名称：

  Iron(III) catalyzed halo-functionalization of alkynes

  摘要：

  Aromatic and aliphatic alkynes can be halo-functionalized to alpha,alpha-dihalodimethyl ketals catalyzed by FeCl3 in excellent yields. MeOH is used as a nucleophilic solvent and N-halosuccinimide as the halogen source for this efficient transformation. The resulting alpha,alpha-dibromodimethyl ketals can be converted to the corresponding alpha,alpha-dibromoketones by treatment with 8% FeCl3 in silica gel. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.05.039

文献信息

• Reactions of terminal alkynes with iodine in methanol
  作者：Victor L. Heasley、Dale F. Shellhamer、Lynn E. Heasley、David B. Yaeger、Gene E. Heasley

  DOI：10.1021/jo01311a020

  日期：1980.11
• m-Iodosylbenzoic acid, a tagged hypervalent iodine reagent for the iodo-functionalization of alkenes and alkynes
  作者：Mekhman S. Yusubov、Roza Ya. Yusubova、Andreas Kirschning、Joo Yeon Park、Ki-Whan Chi

  DOI：10.1016/j.tetlet.2007.12.120

  日期：2008.2

  An efficient and facile method for the iodo-functionalization of alkenes 5 and alkynes 6 by using recyclable ni-iodosylbenzoic acid (2) was developed. The final products can be easily isolated without any chromatographic purification by simple treatment of the crude mixture with an anionic exchange resin. Unreacted m-iodosylbenzoic acid and reduced m-iodobenzoic acid are effectively recovered from the resin by acidification with hydrochloric acid. (c) 2008 Elsevier Ltd. All rights reserved.
• Facile formations of ketals of α, α-dihaloacetophenones
  作者：Pakorn Bovonsombat、Edward McNelis

  DOI：10.1016/s0040-4039(00)74668-5

  日期：1992.7

  Ketals of alpha, alpha-dihaloacetophenones are prepared in high yields from phenylethyne and N-halosuccinimide with catalytic quantities of p-toluenesulfonic acid.
• HEASLEY V. L.; SHELLHAMER D. F.; HEASLEY L. E.; YAEGER D. B.; HEASLEY G. +, J. ORG. CHEM., 1980, 45, NO 23, 4649-4652
  作者：HEASLEY V. L.、 SHELLHAMER D. F.、 HEASLEY L. E.、 YAEGER D. B.、 HEASLEY G. +

  DOI：——

  日期：——
• Iron(III) catalyzed halo-functionalization of alkynes
  作者：Bryant Catano、John Lee、Claudia Kim、David Farrell、Jeffrey L. Petersen、Yalan Xing

  DOI：10.1016/j.tetlet.2015.05.039

  日期：2015.7

  Aromatic and aliphatic alkynes can be halo-functionalized to alpha,alpha-dihalodimethyl ketals catalyzed by FeCl3 in excellent yields. MeOH is used as a nucleophilic solvent and N-halosuccinimide as the halogen source for this efficient transformation. The resulting alpha,alpha-dibromodimethyl ketals can be converted to the corresponding alpha,alpha-dibromoketones by treatment with 8% FeCl3 in silica gel. (C) 2015 Elsevier Ltd. All rights reserved.