Δ⁵-1,3-dioxa-2-thialepin-2-oxide | 6214-15-9

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: Δ⁵-1,3-dioxa-2-thialepin-2-oxide
• 英文别名: 4,7-dihydro-1,3,2-dioxathiepine 2-oxide；4,7-dihydro-1,3,2-dioxathiepine-2-oxide；1,4-but-2-enediol cyclic sulfite；2-butene-1,4-diol sulfite；2-oxo-1,3,2-dioxathiepin；4,7-dihydro-[1,3,2]dioxathiepine 2-oxide
• CAS: 6214-15-9
• 化学式: C₄H₆O₃S
• mdl: MFCD26407687
• 分子量: 134.156
• InChiKey: QAOSUJVCSVOSEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Δ⁵-1,3-dioxa-2-thialepin-2-oxide 在 溴 作用下， 生成 5,6-dibromo-[1,3,2]dioxathiepane 2-oxide
  参考文献：
  名称：

  Riemschneider,R.; Ernst,W., Zeitschrift fur Naturforschung. Teil B. Anorganische Chemie, organische Chemie, Biochemie, Biophysik, Biologie, 1960, vol. 15, p. 552 - 554

  摘要：

  DOI：
• 作为产物：
  描述：

  顺式-1,2-二羟甲基乙烯 在 T406石油添加剂 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到Δ⁵-1,3-dioxa-2-thialepin-2-oxide
  参考文献：
  名称：

  Thionyl Chloride-Benzotriazole in Methylene Chloride: A Convenient Solution for Conversion of Alcohols and Carboxylic Acids Expeditiously into Alkyl Chlorides and Acid Chlorides by Simple Titration

  摘要：

  在干燥的二氯甲烷中，以1:1等量混合的亚硫酰氯和苯并三唑溶液，在室温下能高效地将醇和羧酸分别转化为相应的烷基氯化物和酰氯，且通过简单的滴定法即可获得极佳的产率。

  DOI：

  10.1055/s-1999-2943

文献信息

• Synthesis of Highly Substituted Tetrahydrofurans by Catalytic Polar-Radical-Crossover Cycloadditions of Alkenes and Alkenols
  作者：Jean-Marc M. Grandjean、David A. Nicewicz

  DOI：10.1002/anie.201210111

  日期：2013.4.2

  Light up my ring: The title reaction is catalyzed by an acridinium/phenylmalononitrile photoredox system. A variety of readily available olefins and unsaturated alcohols can be employed to furnish tetrahydrofuran adducts with complete regiocontrol and up to four contiguous stereogenic centers.

  照亮我的戒指：标题反应由cri啶/苯基丙二腈光氧化还原体系催化。可以使用多种容易获得的烯烃和不饱和醇来提供具有完全区域控制和多达四个连续的立体异构中心的四氢呋喃加合物。
• Application of a Chiral Scaffolding Ligand in Catalytic Enantioselective Hydroformylation
  作者：Amanda D. Worthy、Candice L. Joe、Thomas E. Lightburn、Kian L. Tan

  DOI：10.1021/ja107433h

  日期：2010.10.27

  The synthesis of β-amino-aldehydes has been achieved through enantioselective hydroformylation of PMP-protected allylic amines. The reaction is accomplished by using a scalemic scaffolding ligand that covalently and reversibly binds to the substrate. These ligands behave like chiral auxiliaries because they are covalently attached to the substrate during hydroformylation; however, similar to traditional

  β-氨基醛的合成是通过 PMP 保护的烯丙胺的对映选择性加氢甲酰化来实现的。该反应是通过使用与底物共价可逆结合的鳞片支架配体来完成的。这些配体的行为类似于手性助剂，因为它们在加氢甲酰化过程中共价连接到底物上；然而，与传统的不对称配体类似，它们可以以催化量使用。二取代烯烃的直接加氢甲酰化在温和条件（35 °C 和 50 psi CO/H(2)）下进行，Z-烯烃具有优异的对映选择性（高达 93% ee）。
• Methods of producing aminobutene derivatives
  申请人：Fujirebio Inc.

  公开号：US05616711A1

  公开（公告）日：1997-04-01

  A method of producing an aminobutene derivative of formula (I) by allowing a butenol derivative of formula (II) to react with an amide derivative of formula (III) is disclosed. The aminobutene derivative of formula (I) can be deprotected to produce an aminobutene derivative of formula (I-1) or an aminobutene derivative of formula (I-2): ##STR1## The aminobutene derivative of formula (I-A) can also be deprotected to produce the aminobutene derivative of formula (I-B). Any or all of the above aminobutene derivatives are useful as intermediates for producing anti-ulcer drugs, and anti-ulcer drugs having an inhibitory effect on gastric acid secretion based on the antagonism against histamine H.sub.2 receptor.

  本发明公开了一种通过让式（II）的丁醇衍生物与式（III）的酰胺衍生物发生反应来制备式（I）的氨基丁烯衍生物的方法。式（I）的氨基丁烯衍生物可以去保护以产生式（I-1）的氨基丁烯衍生物或式（I-2）的氨基丁烯衍生物：氨基丁烯衍生物的式（I-A）也可以去保护以产生式（I-B）的氨基丁烯衍生物。上述任何或所有氨基丁烯衍生物均可用作制备抗溃疡药物的中间体，以及基于对组胺H.sub.2受体拮抗作用的抗溃疡药物，其具有对胃酸分泌具有抑制作用的效果。
• Regioselective Hydroformylation of Allylic Alcohols
  作者：Thomas E. Lightburn、Omar A. De Paolis、Ka H. Cheng、Kian L. Tan

  DOI：10.1021/ol200782d

  日期：2011.5.20

  hydroformylation of allylic alcohols is reported toward the synthesis of β-hydroxy-acid and aldehyde products. The selectivity is achieved through the use of a ligand that reversibly binds to alcohols in situ, allowing for a directed hydroformylation to occur. The application to trisubstituted olefins was also demonstrated, which yields a single diastereomer product consistent with a stereospecific addition of CO

  据报道，烯丙醇的高度区域选择性加氢甲酰化可用于合成 β-羟基酸和醛产物。选择性是通过使用一种配体来实现的，该配体在原位可逆地结合醇，允许发生定向加氢甲酰化。还证明了三取代烯烃的应用，这产生了与 CO 和氢的立体有择加成一致的单一非对映异构体产品。
• Regioselective Hydroformylation of Sulfonamides using a Scaffolding Ligand
  作者：Amanda D. Worthy、Moriah M. Gagnon、Michael T. Dombrowski、Kian L. Tan

  DOI：10.1021/ol900921e

  日期：2009.7.2

  A highly regioselective hydroformylation of allylic sulfonamides has been developed by employing a catalytic directing group. The reaction tolerates a wide range of electronically and sterically modified olefins, and only 10% of the scaffolding ligand is required to effectively control the regioselectivity.

  通过使用催化导向基团已经开发了烯丙基磺酰胺的高度区域选择性加氢甲酰基化。该反应可耐受多种电子和空间改性的烯烃，仅需10％的支架配体即可有效地控制区域选择性。