1-chloro-1-iodobutane

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: 1-chloro-1-iodobutane
• 英文别名: iodochlorobutane
• 化学式: C₄H₈ClI
• 分子量: 218.465
• InChiKey: FWCCUMCZCQAIMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  6
• 可旋转键数：
  2
• 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-chloro-1-iodobutane 、 丙酮小檗碱 以 乙腈 为溶剂， 生成 21-(1-Iodobutyl)-16,17-dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene;chloride
  参考文献：
  名称：

  Synthesis and structure–activity relationships of novel, substituted 5,6-dihydrodibenzo[a,g]quinolizinium P2X7 antagonists

  摘要：

  Iminium quaternary protoberberine alkaloids (QPA) have been found to be novel P2X(7) antagonists. To assess their structure-activity relationships, these compounds were modified at their R-1 and R-2 groups and assayed for their ability to inhibit the 2'(3')-O-(4-benzoylbenzoyl)-ATP (BzATP)-induced uptake of fluorescent ethidium by HEK-293 cells stably expressing the human P2X(7) receptor, and their ability to inhibit BzATP-induced IL-1 beta release by differentiated THP-1 cells. Compounds 15a and 15d, with alkyl groups at the R-1 position, and especially compound 19h, with the 2-NO2-4,5-dimethoxy-benzyl group at the R-2 position, had potent inhibitory efficacy as P2X(7) antagonists. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.088
• 作为产物：
  描述：

  氯丁烷 在 1-iodo-3,5,5-trimethylhydantoin 作用下， 以 neat (no solvent) 为溶剂， 反应 2.0h， 生成 1-氯-4-碘丁烷 、 1-chloro-1-iodobutane 、 1-chloro-2-iodobutane 、 1-chloro-3-iodobutane
  参考文献：
  名称：

  N-碘酰胺对脂肪族CH键的碘化作用和难分离的N-酰胺基自由基的分离

  摘要：

  与C–H氯化和溴化相反，烷烃的直接碘化是一个巨大的挑战。我们揭示了一种新的N-碘酰胺，它能够直接和有效地对各种环状和无环烷烃进行C–H键碘化，从而以高收率提供碘代烷烃。这是N-碘酰胺在C–H键碘化中的首次应用。该方法对苄基CH键也很有效，从而构成了Wohl-Ziegler碘化反应的缺失形式。通过DFT计算阐明了机械细节，并将使用过的N-碘酰胺衍生的N中心自由基（此过程的关键中间体）在固体氩气基质中进行了基质分离，并通过UV-vis和IR对其进行了表征。光谱学。

  DOI：

  10.1021/acs.joc.7b00557

文献信息

• [EN] PROCESS FOR THE PREPARATION OF N-IODOAMIDES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE N-IODOAMIDES
  申请人：TECHNION RES & DEV FOUNDATION

  公开号：WO2015068159A3

  公开（公告）日：2015-07-16
• Aliphatic C–H Bond Iodination by a <i>N</i>-Iodoamide and Isolation of an Elusive <i>N</i>-Amidyl Radical
  作者：Alexander Artaryan、Artur Mardyukov、Kseniya Kulbitski、Idan Avigdori、Gennady A. Nisnevich、Peter R. Schreiner、Mark Gandelman

  DOI：10.1021/acs.joc.7b00557

  日期：2017.7.21

  Contrary to C–H chlorination and bromination, the direct iodination of alkanes represents a great challenge. We reveal a new N-iodoamide that is capable of a direct and efficient C–H bond iodination of various cyclic and acyclic alkanes providing iodoalkanes in good yields. This is the first use of N-iodoamide for C–H bond iodination. The method also works well for benzylic C–H bonds, thereby constituting

  与C–H氯化和溴化相反，烷烃的直接碘化是一个巨大的挑战。我们揭示了一种新的N-碘酰胺，它能够直接和有效地对各种环状和无环烷烃进行C–H键碘化，从而以高收率提供碘代烷烃。这是N-碘酰胺在C–H键碘化中的首次应用。该方法对苄基CH键也很有效，从而构成了Wohl-Ziegler碘化反应的缺失形式。通过DFT计算阐明了机械细节，并将使用过的N-碘酰胺衍生的N中心自由基（此过程的关键中间体）在固体氩气基质中进行了基质分离，并通过UV-vis和IR对其进行了表征。光谱学。
• Synthesis and structure–activity relationships of novel, substituted 5,6-dihydrodibenzo[a,g]quinolizinium P2X7 antagonists
  作者：Ga Eun Lee、Ho-Sung Lee、So Deok Lee、Jung-Ho Kim、Won-Ki Kim、Yong-Chul Kim

  DOI：10.1016/j.bmcl.2008.11.088

  日期：2009.2

  Iminium quaternary protoberberine alkaloids (QPA) have been found to be novel P2X(7) antagonists. To assess their structure-activity relationships, these compounds were modified at their R-1 and R-2 groups and assayed for their ability to inhibit the 2'(3')-O-(4-benzoylbenzoyl)-ATP (BzATP)-induced uptake of fluorescent ethidium by HEK-293 cells stably expressing the human P2X(7) receptor, and their ability to inhibit BzATP-induced IL-1 beta release by differentiated THP-1 cells. Compounds 15a and 15d, with alkyl groups at the R-1 position, and especially compound 19h, with the 2-NO2-4,5-dimethoxy-benzyl group at the R-2 position, had potent inhibitory efficacy as P2X(7) antagonists. (C) 2008 Elsevier Ltd. All rights reserved.