trans-(2SR,4SR)-2-benzyl-4-phenyl-1,3-dioxolane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-(2SR,4SR)-2-benzyl-4-phenyl-1,3-dioxolane
• 英文别名: trans-2-benzyl-4-phenyl-1,3-dioxolane；(2R,4R)-2-benzyl-4-phenyl-1,3-dioxolane
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: WIAZXGHBTOASSQ-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  氧化苯乙烯 在 sodium hydrogen sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以48%的产率得到trans-(2SR,4SR)-2-benzyl-4-phenyl-1,3-dioxolane
  参考文献：
  名称：

  Ring opening of epoxides with NaHSO4: isolation of β-hydroxy sulfate esters and an effective synthesis for trans-diols

  摘要：

  Sodium hydrogen sulfate (NaHSO4) was observed to be highly effective as a reagent or catalyst in the ring-opening reactions of epoxides under mild conditions. Reaction of epoxides with NaHSO4 gave isolable P-hydroxy sulfate esters and vicinal diols. Experimenting with different epoxides, the study investigated the scope of the ring-opening reaction. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.092

文献信息

• Iodine-catalyzed tandem synthesis of terminal acetals and glycol mono esters from olefins
  作者：Macharla Arun Kumar、Peraka Swamy、Mameda Naresh、Marri Mahender Reddy、Chozhiyath Nappunni Rohitha、Sripadi Prabhakar、Akella Venkata Subrahmanya Sarma、Joseph Richard Prem Kumar、Nama Narender

  DOI：10.1039/c3cc38085h

  日期：——

  A new metal-free protocol is described for the synthesis of terminal acetals by tandem oxidative rearrangement of olefins using oxone as an oxidant in the presence of iodine. Moreover, a one-pot procedure for the preparation of glycol mono esters from olefins is also presented for the first time using the same reagent system.

  描述了一种新的无金属方案，该方案通过在碘存在下使用氧酮作为氧化剂，通过烯烃的串联氧化重排来合成末端缩醛。此外，首次提出了使用相同的试剂系统从烯烃制备二醇单酯的一锅法程序。
• An unexpected 1,2-hydride shift in phosphoric acid-promoted cyclodimerization of styrene oxides under solvent-free conditions. A synthetic route towards 2,4-disubstituted 1,3-dioxolanes
  作者：Ofentse Mazimba、Runner R. Majinda、Ishmael B. Masesane

  DOI：10.1016/j.tetlet.2009.08.044

  日期：2009.10

  A 1,2-hydride shift in the phosphoric acid-promoted cyclodimerization of styrene oxide and its chloro derivatives under solvent-free conditions leading to 2,4-disubstituted 1,3-dioxolanes is described. Methoxy substituents on the aromatic ring of the styrene oxide prevent the 1,2-hydride shift reaction leading to substituted 1,4-dioxanes. A possible mechanism for the formation of the 1,3-dioxolanes

  描述了在无溶剂条件下磷酸促进的苯乙烯氧化物及其氯衍生物的环二聚反应中的1,2-氢化物移位，从而导致2,4-二取代的1,3-二氧戊环。氧化苯乙烯的芳环上的甲氧基取代基可防止1,2-氢化物转移反应，从而导致取代的1,4-二恶烷。提出了一种可能的机制，以形成1，3-二氧戊环。
• Lewis-Acid-Catalysed Tandem Meinwald Rearrangement/Intermolecular [3+2]-Cycloaddition of Epoxides with Donor-Acceptor Cyclopropanes: Synthesis of Functionalized Tetrahydrofurans
  作者：Ashok Kumar Pandey、Asit Ghosh、Prabal Banerjee

  DOI：10.1002/ejoc.201403590

  日期：2015.4

  A Lewis-acid-catalysed tandem Meinwald rearrangement/[3+2]-cycloaddition of epoxides with donor–acceptor cyclopropanes to synthesize varieties of cis-2,5-aryl-benzyl-substituted tetrahydrofurans is described. An enantioselective version of the same transformation was achieved using an InCl3–PyBOX catalyst system.

  描述了路易斯酸催化的串联 Meinwald 重排/[3+2]-环氧化物与供体-受体环丙烷的环加成反应，以合成各种顺式-2,5-芳基-苄基取代的四氢呋喃。使用 InCl3-PyBOX 催化剂系统实现了相同转化的对映选择性版本。
• Mazimba, Ofentse; Majinda, Runner R.; Masesane, Ishmael B., Bulletin of the Chemical Society of Ethiopia, 2011, vol. 25, # 2, p. 299 - 304
  作者：Mazimba, Ofentse、Majinda, Runner R.、Masesane, Ishmael B.

  DOI：——

  日期：——