2-(5-Hydroxypentan-1-yl)-1,3-dithiane | 118794-78-8

• 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-(5-Hydroxypentan-1-yl)-1,3-dithiane
• 英文别名: 5-(1,3-dithian-2-yl)pentan-1-ol
• CAS: 118794-78-8
• 化学式: C₉H₁₈OS₂
• 分子量: 206.373
• InChiKey: WPBNNYOXBXRTHI-UHFFFAOYSA-N

物化性质

• 沸点：
  333.4±22.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5-Hydroxypentan-1-yl)-1,3-dithiane 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.25h， 生成 3-[2-[4-(4-methoxy-benzyloxy)butyl][1,3]dithiane-2-yl]hexahydro-3a,6-ethanoinden-1-one
  参考文献：
  名称：

  一种不寻常的分子内Diels–Alder方法对茂铁晶体V

  摘要：

  分子内Diels–Alder反应通常用于合成多环天然产物，但使用醛作为亲二烯体是分子内环加成反应中一个未开发的方面。该反应的分子内性质允许使用醛作为亲二烯体而无需使用高度活化的二烯，这通常是与醛的分子间狄尔斯-阿尔德反应所必需的。利用这种新化学方法探索了合成毛晶V的合成途径。

  DOI：

  10.1016/j.tetlet.2013.01.075
• 作为产物：
  描述：

  6-(tetrahydro-2H-pyran-2-yloxy)hexyl acetate 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-(5-Hydroxypentan-1-yl)-1,3-dithiane
  参考文献：
  名称：

  Differentiation between carbonyls and acetals in 1,3-dithiane and 1,3-dithiolane synthesis catalyzed by organotin triflates

  摘要：

  Carbonyls and acetals are converted to 1,3-dithianes and -dithiolanes upon treatment with 2-stanna-1,3-dithianes and -dithiolanes under catalysis by organotin triflates. In these competition reactions, various types of carbonyls and acetals are differentiated. Aldehydes react preferentially over ketones, but the preference is completely reversed in the competition reactions between the corresponding acetals and ketals. The reactivity of aliphatic aldehydes is greater than that of the acetals of aliphatic aldehydes and ketones. Conversely, an aromatic acetal is more reactive than its parent aldehyde. In the competition between aromatic and aliphatic aldehydes, the reaction of the latter predominates. However, aromatic acetals react preferentially over aliphatic acetals. Ketones of different types are also differentiated. No such discrimination can be achieved by conventional methods. Organotin triflates are capable of detecting subtle differences in the reactivity of carbonyls and acetals. Such unique differentiation can be explained in terms of the dependence of the reaction path on the substrate: the reactions of carbonyls are initiated by coordination to tin, whereas the reactions of acetals proceed via oxocarbenium ion intermediates.

  DOI：

  10.1021/jo00070a038

文献信息

• Activation and synthetic applications of thiostannanes. Conversion of aldehydes and acetals into 1,3-dithianes with high chemodifferentiation
  作者：Tsuneo Sato、Enji Yoshida、Takamichi Kobayashi、Junzo Otera、Hitosi Nozaki

  DOI：10.1016/s0040-4039(00)80396-2

  日期：1988.1

  Novel method for transforming aldehydes and acetals into 1,3-dithianes has been achieved with the aid of organotin thioalkoxides and organotin triflates. Under these reaction conditions, various acid-sensitive groups are tolerated. Differentiation between aromatic or aliphatic aldehydes and acetals has been realized.

  借助于有机锡硫代醇盐和有机锡三氟甲磺酸酯，已经实现了将醛和乙缩醛转化为1，3-二硫杂环己烷的新方法。在这些反应条件下，可以耐受各种酸敏感性基团。已经实现了芳族或脂族醛与缩醛之间的区分。
• A Mild, Chemoselective Protocol for the Removal of Thioketals and Thioacetals Mediated by Dess−Martin Periodinane
  作者：Neil F. Langille、Les A. Dakin、James S. Panek

  DOI：10.1021/ol027518n

  日期：2003.2.1

  development of a useful procedure for the removal of thioacetals and thioketals using Dess-Martin periodinane (DMP) reagent. In contrast to existing methods, this protocol offers general reactivity, compatibility with a wide range of functional groups, and convenient reaction times. Also discussed are chemoselectivity experiments involving functionalities that may be subject to oxidation by DMP, qualitative

  [反应：见正文]本文介绍了使用Dess-Martin高碘烷（DMP）试剂去除硫缩醛和硫缩酮的有用方法的开发。与现有方法相比，该协议具有一般的反应性，与各种官能团的相容性以及方便的反应时间。还讨论了化学选择性实验，涉及的功能可能会被DMP氧化，底物对水解速率的定性影响以及硫代乙缩醛向乙缩醛的直接转化。
• Organocatalyst-mediated enantioselective intramolecular Michael addition of aldehydes to vinyl sulfones
  作者：Chloée Bournaud、Estelle Marchal、Adrien Quintard、Sarah Sulzer-Mossé、Alexandre Alexakis

  DOI：10.1016/j.tetasy.2010.03.043

  日期：2010.7

  Chiral amines with a hydrogen bond donor promote the intramolecular conjugate addition of aldehydes to vinyl sulfones. Chiral cyclic sulfone-aldehydes are obtained in good yields with an ee of up to 82%. (C) 2010 Elsevier Ltd. All rights reserved.
• A simple method of dethioacetalization
  作者：Gilbert Stork、Kang Zhao

  DOI：10.1016/s0040-4039(00)95181-5

  日期：1989.1
• STORK, GILBERT;ZHAO, KANG, TETRAHEDRON LETT., 30,(1989) N, C. 287-290
  作者：STORK, GILBERT、ZHAO, KANG

  DOI：——

  日期：——