4-(p-toluenesulfonyloxymethyl)-2-phenyl-1,3-dioxane | 127945-31-7

• 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: 4-(p-toluenesulfonyloxymethyl)-2-phenyl-1,3-dioxane
• 英文别名: [(2R,4R)-2-phenyl-1,3-dioxan-4-yl]methyl 4-methylbenzenesulfonate
• CAS: 127945-31-7
• 化学式: C₁₈H₂₀O₅S
• 分子量: 348.42
• InChiKey: DRIXRSKYXISMDH-SJLPKXTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(p-toluenesulfonyloxymethyl)-2-phenyl-1,3-dioxane 在 copper(l) iodide 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (S)-3-benzyloxy-1-dodecanol
  参考文献：
  名称：

  全合成（2 S，3 R，5 S）-（-）-2,3-二羟基四十二烷-5-油酸酯，这是一种由独角兽铱生产的新型生物活性δ-内酯

  摘要：

  （2的第一全合成小号，3 - [R，5小号（ - - ） - ）2,3- dihydroxytetradecan -5-内酯（1）中，由所产生的新的生物活性δ内酯Seiridium unicome，从（完成ř）-苹果酸。关于确定1的绝对构型，还由D-葡萄糖合成了（2 R，3 S，5 R）-（+）-2，3-二羟基十四烷-5-内酯（ent-1）。

  DOI：

  10.1016/s0040-4020(99)00056-3
• 作为产物：
  描述：

  (R)-(+)-1,2,4-丁三醇 、 苯甲醛 、 对甲苯磺酰氯 在 吡啶 、 三氟乙酸 作用下， 生成 4-(p-toluenesulfonyloxymethyl)-2-phenyl-1,3-dioxane
  参考文献：
  名称：

  对映异构体C 4-合成β-羟基黄油，对映体和对映体†

  摘要：

  具有四个C原子和两个或三个来自β-羟基丁酸，苹果酸和酒石酸的官能团的对映体纯合成构件

  DOI：

  10.1002/hlca.19810640523

文献信息

• Synthesis and structure–activity relationship of p-carborane-based non-secosteroidal vitamin D analogs
  作者：Shinya Fujii、Atsushi Kano、Chalermkiat Songkram、Hiroyuki Masuno、Yoshiyuki Taoda、Emiko Kawachi、Tomoya Hirano、Aya Tanatani、Hiroyuki Kagechika

  DOI：10.1016/j.bmc.2014.01.015

  日期：2014.2

  different from classical secosteroidal vitamin D analogs. Here, we report systematic synthesis and activity evaluation of carborane-based non-secosteroidal vitamin D analogs. The structure–activity relationships of carborane derivatives are different from those of secosteroidal vitamin D derivatives, and in particular, the length and the substituent position of the dihydroxylated side chain are rather

  1α，25-二羟基维生素D 3 [1α，25（OH）2 D 3：1 ]是核维生素D受体（VDR）的特定调节剂，新型维生素D类似物是多种临床应用的治疗候选物。我们最近开发了带有p的非类固醇VDR激动剂-碳硼烷笼（含碳的硼簇）作为疏水核结构。这些碳硼烷衍生物在结构上与经典的类固醇维生素D类似物完全不同。在这里，我们报告基于碳硼烷的非secosteroidal维生素D类似物的系统合成和活性评估。碳硼烷衍生物的结构-活性关系与类固醇维生素D衍生物的结构-活性关系不同，特别是，二羟基化侧链的长度和取代基位置在碳硼烷衍生物中相当灵活。此处介绍的结构-活性关系应有助于开发用于临床应用的非类固醇维生素D类似物。
• New and Concise Approach to (<i>R</i>)-<font>α</font>-Lipoic Acid
  作者：Zhen Wei、Hong-Qiao Lan、Jian-Feng Zheng、Pei-Qiang Huang

  DOI：10.1080/00397910802431073

  日期：2009.1.28

  Abstract A concise enantiospecific synthesis of (S)-6,8-bis(methylsulfonyloxy)-octanoic acid (2), a ready precursor of (R)-(+)-α-lipoic acid (1), is reported. The key step of the synthesis is the coupling of the tosylate derived from (R)-malic acid with phenylpropyl magnesium bromide. A recently reported green procedure was used for the oxidative unmasking of the phenyl group, used as a latent carboxyl

  摘要报道了 (S)-6,8-双(甲基磺酰氧基)-辛酸 (2) 的简明对映特异性合成，这是 (R)-(+)-α-硫辛酸 (1) 的现成前体。合成的关键步骤是将衍生自 (R)-苹果酸的甲苯磺酸酯与苯丙基溴化镁偶联。最近报道的绿色程序用于苯基的氧化暴露，用作潜在的羧基。
• Fujii, Shinya; Masuno, Hiroyuki; Taoda, Yoshiyuki, Journal of the American Chemical Society, 2011, vol. 133, p. 20933 - 20941
  作者：Fujii, Shinya、Masuno, Hiroyuki、Taoda, Yoshiyuki、Kano, Atsushi、Wongmayura, Angsuma、et al.

  DOI：——

  日期：——
• Isolation, structural determination, and total synthesis of a new biologically active δ-lactone produced by Seiridium unicorne
  作者：Hiroaki Toshima、Ayako Watanabe、Hiroji Sato、Akitami Ichihara

  DOI：10.1016/s0040-4039(98)02103-0

  日期：1998.12

  The structure of a new biologically active delta-lactone, produced by Seiridium unicome, was determined to be (2S,3R,5S)-(-)-2,3-dihydroxytetradecan-5-olide. The relative configuration was elucidated from NMR experiments. The synthesis of the enantiomer from D-glucose revealed the absolute configuration. The total synthesis of the natural form was also achieved from (R)-malic acid. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Novel vitamin D receptor ligands bearing a spherical hydrophobic core structure—Comparison of bicyclic hydrocarbon derivatives with boron cluster derivatives
  作者：Angsuma Wongmayura、Shinya Fujii、Shigeru Ito、Atsushi Kano、Yoshiyuki Taoda、Emiko Kawachi、Hiroyuki Kagechika、Aya Tanatani

  DOI：10.1016/j.bmcl.2011.12.137

  日期：2012.2

  Vitamin D receptor (VDR) is a nuclear receptor for 1 alpha, 25-dihydroxyvitamin D-3 (1 alpha, 25(OH)(2)D-3), and is an attractive target for multiple clinical applications. We recently developed novel non-secosteroidal VDR ligands bearing a hydrophobic p-carborane cage, thereby establishing the utility of this spherical hydrophobic core structure for development of VDR ligands. Here, we synthesized two series of novel non-secosteroidal VDR ligands with different spherical hydrophobic cores, that is, bicyclo[2.2.2] octane derivatives and p-carborane derivatives, and compared their biological activities in order to examine the difference between the interactions of the C-H hydrocarbon surface and the B-H carborane surface with the receptor. Carborane derivatives exhibited more potent differentiation-inducing activity toward HL-60 cells than did the corresponding bicyclo[2.2.2] octane derivatives. These results suggest that the hydrophobic carborane cage may interact more efficiently than the hydrocarbons with the hydrophobic surface of VDR. This finding further supports the view that carborane structure is a promising option for drug development. (C) 2012 Elsevier Ltd. All rights reserved.