trans-3,4-didehydro-3,4-dideoxy-1,2:5,6-di-O-isopropylidene-D-threo-hexitol | 53777-24-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-3,4-didehydro-3,4-dideoxy-1,2:5,6-di-O-isopropylidene-D-threo-hexitol
• 英文别名: 3,4-dideoxy-1,2:5,6-di-O-isopropylidene-erythro-hex-E-3-enitol；(4R)-4-[(E)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethenyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 53777-24-5
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: OJKJTRYVWJHGDH-GMCFVEKCSA-N

物化性质

• 沸点：
  299.6±35.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-3,4-didehydro-3,4-dideoxy-1,2:5,6-di-O-isopropylidene-D-threo-hexitol 在 吡啶 、 sodium methylate 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 26.33h， 生成 2,5-di-O-acetyl-3,4-dideoxy-1,6-di-O-p-tolylsulfonyl-erythro-hex-E-3-enitol
  参考文献：
  名称：

  Synthesis of 1,2:5,6-dianhydro-3,4-dideoxy-erythro- and D-threo-hexitol and their E-3-ENE derivatives

  摘要：

  DOI：

  10.1016/s0008-6215(00)85364-1
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3,4-bis-O-(methylsulfonyl)-D-glucitol 在 sodium iodide 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以36%的产率得到trans-3,4-didehydro-3,4-dideoxy-1,2:5,6-di-O-isopropylidene-D-threo-hexitol
  参考文献：
  名称：

  Synthesis of 1,2:5,6-dianhydro-3,4-dideoxy-erythro- and D-threo-hexitol and their E-3-ENE derivatives

  摘要：

  DOI：

  10.1016/s0008-6215(00)85364-1

文献信息

• Synthesis of C2-symmetric analogues of 4-(pyrrolidino)pyridine: new chiral nucleophilic catalysts
  作者：Alan C. Spivey、Adrian Maddaford、Tomasz Fekner、Alison J. Redgrave、Christopher S. Frampton

  DOI：10.1039/b004704j

  日期：——

  The syntheses of a series of enantiomerically pure C2-symmetric 4-(pyrrolidino)pyridine (PPY) derivatives by SNAr of 4-halo-/4-phenoxypyridines and by cyclocondensation from 4-aminopyridine are described. Preliminary results pertaining to their use as catalysts for acylative kinetic resolution of 1-phenylethanol are also presented. A single-crystal X-ray analysis of PPY If is reported.

  通过4-卤代/4-苯氧基吡啶的SNAr反应以及4-氨基吡啶的环化缩合反应，合成了一系列手性纯的C2对称4-(吡咯烷基)吡啶(PPY)衍生物。同时，初步结果表明它们可用作1-苯乙醇的酰基动力学拆分催化剂。此外，还报道了PPY If的单晶X射线分析。
• Efficient Conversion of Vicinal Diols to Alkenes by Treatment of the Corresponding Dimesylates with a Catalytic, Minimally Fluorous, Recoverable Diaryl Diselenide and Sodium Borohydride
  作者：David Crich、Santhosh Neelamkavil、Fernando Sartillo-Piscil

  DOI：10.1021/ol0066532

  日期：2000.12.1

  In conjunction with sodium borohydride as stoichiometric reagent a catalytic quantity of bis(4-perfluorohexylphenyl) diselenide converts vicinal dimesylates to the corresponding alkenes in good yield on warming in ethanol. The diselenide is recovered in high yield by continuous fluorous extraction.

  与作为化学计量试剂的硼氢化钠一起，催化量的双（4-全氟己基苯基）二硒化物在乙醇中升温时，可以将邻位二甲基化产物以良好的产率转化为相应的烯烃。通过连续的氟萃取以高收率回收二硒化物。
• Facile Synthesis of Optically Active Tertiary Alcohol Building Blocks by Stereospecific C–H Insertion Reaction of Dichlorocarbene with Secondary Alcohol Derivatives
  作者：Yukio Masaki、Hideki Arasaki、Motoo Shiro

  DOI：10.1246/cl.2000.1180

  日期：2000.10

  Stereospecific C–H insertion of dichlorocarbene generated from a system CHCl3/50%NaOH/cetyltrimethylammonium chloride (as a PTC) proceeded at the carbinol carbon in the reaction of chiral secondary alcohol derivatives to provide α-dichloromethylated tertiary alcohol derivatives with complete retention of configuration.

  由 CHCl3/50%NaOH/十六烷基三甲基氯化铵（作为 PTC）系统生成的二氯卡宾的立体特异性 C-H 插入在手性仲醇衍生物反应中的甲醇碳上进行，以提供完全保留构型的 α-二氯甲基化叔醇衍生物.
• Synthesis of novel analogues of (+)-varitriol via olefin cross-metathesis reaction
  作者：Lingaiah Nagarapu、Venkateswarlu Paparaju、Apuri Satyender

  DOI：10.1016/j.bmcl.2008.02.062

  日期：2008.4

  Novel analogues of (+)-varitriol have been synthesized via olefin cross-metathesis reaction using Grubb's catalyst. Newly synthesized compounds were screened for cytotoxicity and they showed mild activity against RAW264.7 and HT29 cell lines.

  （+）-varitriol的新型类似物已通过使用格鲁布（Grubb）催化剂的烯烃交叉复分解反应合成。筛选了新合成的化合物的细胞毒性，并且它们对RAW264.7和HT29细胞系表现出适度的活性。