2-iodomethyl-1,3-dioxolane | 41031-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 2-iodomethyl-1,3-dioxolane
• 英文别名: 2-(Iodomethyl)-1,3-dioxolane
• CAS: 41031-93-0
• 化学式: C₄H₇IO₂
• 分子量: 214.003
• InChiKey: UCMYHULDFYFCNY-UHFFFAOYSA-N

物化性质

• 沸点：
  84 °C(Press: 12 Torr)
• 密度：
  1.933±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  2-iodomethyl-1,3-dioxolane 、 (+)-(S)-2-(2-methylbutyl)-2-thiazoline 在 正丁基锂 作用下， 生成 (3RS,4S)-4-methyl-3-(2-thiazoline-2-yl)-1,1-ethanediyldioxyhexane
  参考文献：
  名称：

  Chelucci, Giorgio; Soccolini, Franco, Synthetic Communications, 1987, vol. 17, # 4, p. 477 - 484

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴甲基-1,3-二氧戊烷 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以85%的产率得到2-iodomethyl-1,3-dioxolane
  参考文献：
  名称：

  Concise Synthetic Approaches for the Laurencia Family: Formal Total Syntheses of (±)-Laurefucin and (±)-E- and (±)-Z-Pinnatifidenyne

  摘要：

  Herein is presented a cohesive strategy to rapidly fashion diverse members of the lauroxocane family of natural products, leading to the shortest syntheses of any member to date. These efforts include racemic formal total syntheses of laurefucin and E- and Z-pinnatifidenyne as well as a facile preparation of the oxocene core of 3E-dehydrobromolaurefucin. The key elements of the design are novel diastereoselective ring-expanding bromoetherifications of tetrahydrofurans triggered by a unique bromonium source (BDSB, Et2SBr center dot SbBrCl5) and strategically positioned nucleophilic traps, where altering the identity and position of these traps affords diverse functionality on the eight-membered ring backbone. Its biogenetic relevance is also discussed in light of the range of substrates that successfully undergo this key rearrangement.

  DOI：

  10.1021/ja3076988

文献信息

• Chiral Alkyl Amine Synthesis via Catalytic Enantioselective Hydroalkylation of Enecarbamates
  作者：Deyun Qian、Srikrishna Bera、Xile Hu

  DOI：10.1021/jacs.0c11630

  日期：2021.2.3

  Chiral alkyl amines are omnipresent as bioactive molecules and synthetic intermediates. The catalytic and enantioselective synthesis of alkyl amines from readily accessible precursors is challenging. Here we develop a nickel-catalyzed hydroalkylation method to assemble a wide range of chiral alkyl amines from enecarbamates (N-Cbz-protected enamines) and alkyl halides with high regio- and enantioselectivity

  手性烷基胺作为生物活性分子和合成中间体无处不在。从容易获得的前体催化和对映选择性合成烷基胺具有挑战性。在这里，我们开发了一种镍催化的加氢烷基化方法，以从具有高区域选择性和对映选择性的烯氨基甲酸酯（N-Cbz 保护的烯胺）和烷基卤化物中组装各种手性烷基胺。该方法适用于未活化和活化的烷基卤化物，并且能够生产具有两个最小差异的 α-烷基取代基的对映异构富集胺。温和的条件导致高官能团耐受性，这在许多天然产物和药物分子的后产物官能化以及手性构建块和生物活性化合物的关键中间体的合成中得到证明。
• A Facile Synthesis of 3-Substituted Glutaraldehyde Monoacetals from Nitriles
  作者：Giorgio Chelucci

  DOI：10.1055/s-1991-26497

  日期：——

  3-Substituted glutaraldehyde monoacetals 7 have been prepared in 48-58% overall yield, consecutively by the alkylation of nitriles, first with 2-bromo-1,1-diethoxyethane (2) and then with 2-iodomethyl-1,3-dioxolane (4), followed by removal of the cyano group and selective hydrolysis of the diethyl acetal function.

  3-取代的戊二醛单乙缩醛7已通过连续步骤以48-58%的总产率制备，首先通过氰基与2-溴-1,1-二乙氧基乙烷（2）的烷基化反应，随后与2-碘甲基-1,3-二氧杂环戊烷（4）反应，接着去除氰基并选择性水解二乙基乙缩醛官能团。
• Intramolecular [3 + 2] annulation of allenylsilane-enes: Direct synthesis of highly strained trans-fused 5/5 ring systems
  作者：Na Lv、Jing-Chun Han、Peng Zhang、Yu-Rou Huang、Zi-Xun Xu、Kunhua Xu、Xin-Feng Wang、Xin Li、Lung Wa Chung、Chuang-Chuang Li

  DOI：10.1016/j.chempr.2023.08.009

  日期：2024.1

  The first asymmetric total synthesis of β-funebrene, which contains a highly strained -fused 5/5 ring system, has been achieved. The synthetically challenging and multi-functionalized -fused 5/5 ring systems were diastereoselectively and efficiently constructed by the first intramolecular [3 + 2] annulation reaction of allenylsilane-enes. This simple, direct transformation shows broad substrate scope

  首次实现了含有高张力稠合5/5环体系的β-funebrene的不对称全合成。通过丙二烯基硅烷-烯的第一个分子内[3 + 2]环化反应，非对映选择性且高效地构建了具有合成挑战性的多功能稠合5/5环系统。这种简单、直接的转化显示了广泛的底物范围并且具有立体定向性。因此，这项工作代表了第一个从无环前体直接合成稠合 5/5 环系统的立体选择性方法。
• Chelucci, Giorgio; Giacomelli, Giampaolo; Scano, Gianfranco, Gazzetta Chimica Italiana, 1991, vol. 121, # 2, p. 107 - 108
  作者：Chelucci, Giorgio、Giacomelli, Giampaolo、Scano, Gianfranco

  DOI：——

  日期：——
• Oxazolines. IX. Synthesis of homologated acetic acids and esters
  作者：A. I. Meyers、Davis L. Temple、Robert L. Nolen、Edward D. Mihelich

  DOI：10.1021/jo00932a022

  日期：1974.9