2-allyl-1,3-dithiane | 63382-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: 2-allyl-1,3-dithiane
• 英文别名: 2-allyl-[1,3]dithiane；2-prop-2-enyl-1,3-dithiane
• CAS: 63382-29-6
• 化学式: C₇H₁₂S₂
• 分子量: 160.304
• InChiKey: UPJVIMXKITWLOO-UHFFFAOYSA-N

物化性质

• 沸点：
  71-72 °C(Press: 0.1 Torr)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-allyl-1,3-dithiane 在 正丁基锂 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 11.0h， 生成 (2R,4S)-5-(2-allyl-1,3-dithian-2-yl)-4-methoxypentan-2-ol
  参考文献：
  名称：

  The first stereoselective synthesis of dendrodolide A

  摘要：

  The first stereoselective total synthesis of natural product, dendrodolide A (1) is described from readily available (R)-propylene oxide and 3-buten-1-ol as starting materials. The synthesis was achieved in 10 steps with an overall yield of 19.1%. The key steps involved in the synthesis are Jacobsen hydrolytic kinetic resolution, epoxide ring opening with 2-allyl-1, 3-dithiane, Yamaguchi esterification, and ring-closing metathesis (RCM). 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.11.044
• 作为产物：
  描述：

  在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 2-allyl-1,3-dithiane
  参考文献：
  名称：

  Method for sulfide S-benzylation or S-allylation using trimethylsilyl triflate activated benzyl or allyl ethers

  摘要：

  DOI：

  10.1021/jo00329a048

文献信息

• Enantioselective synthesis of aurisides A and B, cytotoxic macrolide glycosides of marine origin
  作者：Kiyotake Suenaga、Hiroshi Hoshino、Takanori Yoshii、Kazunori Mori、Hiroki Sone、Yuhki Bessho、Akira Sakakura、Ichiro Hayakawa、Kiyoyuki Yamada、Hideo Kigoshi

  DOI：10.1016/j.tet.2006.05.077

  日期：2006.8

  The enantioselective synthesis of aurisides A and B, macrolide glycosides of marine origin, was achieved by a convergent approach. The C1–C9 segment 4 was prepared from (R)-pantolactone, and the C10–C17 segment 14 was synthesized from (R)-glycidyl trityl ether. The Nozaki–Hiyama–Kishi reaction between 4 and 14 and subsequent reactions gave seco acid 10, which was converted into the aglycon (3) of aurisides

  通过收敛的方法实现了Aurisides A和B（海洋来源的大环内酯糖苷）的对映选择性合成。C1-C9段4由（R）-泛内酯制备，C10-C17段14由（R）-缩水甘油基三苯甲基醚合成。4至14之间的Nozaki–Hiyama–Kishi反应及随后的反应产生了癸二酸10，其通过构建14元内酯和溴取代的共轭二烯而转化为耳苷的糖苷（3）。糖苷配基的糖基化反应提供了苷A和B.
• Atom-transfer radical addition of fluoroalkyl bromides to alkenes <i>via</i> a photoredox/copper catalytic system
  作者：Vladislav S. Kostromitin、Artem A. Zemtsov、Vladimir A. Kokorekin、Vitalij V. Levin、Alexander D. Dilman

  DOI：10.1039/d1cc01609a

  日期：——

  A method for the addition of fluorinated alkyl bromides to alkenes is described. The reaction proceeds under visible light irradiation in the presence of two catalysts: Ir(ppy)3 and N-heterocyclic carbene ligated copper bromide (IMesCuBr). The role of the iridium photocatalyst is to generate the fluoralkyl radical, while the copper promotes formation of the carbon–bromine bond.

  描述了将氟化烷基溴加成至烯烃的方法。该反应在可见光辐射下，在两种催化剂（Ir（ppy）3和N-杂环卡宾连接的溴化铜（IMesCuBr））的存在下进行。铱光催化剂的作用是产生氟烷基，而铜则促进碳-溴键的形成。
• Total synthesis, biological evaluation of dendrodolides A–D and their analogues
  作者：B. Poornima、A. Venkanna、B. Swetha、Karthik reddy Kamireddy、Bandi Siva、V.S. Phani Babu、Ramesh Ummanni、K. Suresh Babu

  DOI：10.1016/j.tet.2016.06.042

  日期：2016.8

  A concise total synthesis of dendrodolides A–D (1–4) has been accomplished in 10 steps from commercially available (R)-propylene oxide and 3-buten-1-ol as starting materials. The key steps involved in the synthesis are Jacobsen hydrolytic kinetic resolution, epoxide ring opening with 2-allyl-1, 3-dithiane, Yamaguchi esterification and ring-closing metathesis (RCM). In addition, a series of ester derivatives

  以市售的（R）-环氧丙烷和3-丁烯-1-醇为起始原料，经过10个步骤完成了Dendrodolides A–D（1-4）的简明全合成。合成中涉及的关键步骤是Jacobsen水解动力学拆分，2-烯丙基-1、3-二噻吩的环氧开环，山口酯化和闭环复分解（RCM）。此外，利用山口酯化在树突状多核苷酸核心的C-3位制备了一系列酯衍生物，并筛选了它们对抗癌细胞系的功效。
• Oxidative Generation of Thioalkyl Cations from 2-Tributylstannyl-1,3-dithianes and 1-(Tributylstannyl)alkyl Sulfides and Their Reactions with Olefinic Nucleophiles
  作者：Koichi Narasaka、Noriyoshi Arai、Tatsuo Okauchi

  DOI：10.1246/bcsj.66.2995

  日期：1993.10

  2-Tributylstannyl-1,3-dithianes and 1-(tributylstannyl)alkyl sulfides are oxidized with ammonium hexanitratocerate(IV) or ferrocenium hexafluorophosphate to generate their cation radicals, which dissociate into the carbocations and tributylstannyl radical. The carbocations thus generated react with olefinic nucleophiles to afford the corresponding addition products in good yield.

  2-三丁基甲锡烷基-1,3-二噻烷和 1-(三丁基甲锡烷基) 烷基硫化物被六硝酸铵 (IV) 或六氟磷酸二茂铁氧化生成它们的阳离子自由基，其离解成碳阳离子和三丁基锡烷基自由基。由此产生的碳正离子与烯烃亲核试剂反应，以良好的产率得到相应的加成产物。
• The directed Pauson-Khand reaction
  作者：Marie E. Krafft、Carmelinda A. Juliano、Ian L. Scott、Colin Wright、Michael D. McEachin

  DOI：10.1021/ja00005a038

  日期：1991.2

  The regioselectivity of the cobalt-mediated cocyclization of an alkene, an alkyne, and carbon monoxide has been shown to be directed by the use of a soft atom, either sulfur or nitrogen, tethered to the alkene partner by a carbon chain. Direction from the homoallylic position is more efficient thant from the allylic or bishomoallylic position. A rationale is proposed to explain this observation. Studies

  钴介导的烯烃、炔烃和一氧化碳共环化的区域选择性已被证明是通过使用一个软原子（硫或氮）来指导的，硫或氮通过碳链连接到烯烃伙伴上。来自同位烯丙基位置的方向比来自烯丙基或双烯丙基位置的方向更有效。提出了一个基本原理来解释这一观察结果。研究了不同烷基对硫和氮的影响以及其他修饰