ethyl 2,2-dimethyl-3-(4-toluenesulfonyloxy)butanoate | 316148-56-8

• 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: ethyl 2,2-dimethyl-3-(4-toluenesulfonyloxy)butanoate
• 英文别名: ethyl 2,2-dimethyl-3-(tosyloxy)butanoate；Ethyl 2,2-dimethyl-3-(4-methylphenyl)sulfonyloxybutanoate
• CAS: 316148-56-8
• 化学式: C₁₅H₂₂O₅S
• 分子量: 314.403
• InChiKey: TVGAEMDSHMCGLN-UHFFFAOYSA-N

物化性质

• 熔点：
  38-39 °C
• 沸点：
  421.7±28.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2,2-dimethyl-3-(4-toluenesulfonyloxy)butanoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 36.0h， 生成 2,2-二甲基-3-丁烯酸
  参考文献：
  名称：

  Total Synthesis of the Potent HIF-1 Inhibitory Antitumor Natural Product, (8R)-Mycothiazole, via Baldwin–Lee CsF/CuI sp³–sp²-Stille Cross-Coupling. Confirmation of the Crews Reassignment

  摘要：

  A convenient asymmetric total synthesis of the potent HIF-1 inhibitory antitumor natural product, (-)- or (+)-(8R)-mycothiazole (1), is described. Not only does our synthesis confirm the 2006 structural reassignment made by Crews (Crews, P., et al. J. Nat. Prod. 2006, 69, 145), it revises the [a]p data previously reported for this molecule in MeOH from -13.7 degrees to +42.3 degrees. The newly developed route to (8R)-1 sets the C(8)-OH stereocenter via Sharpless AE/2,3-epoxy alcohol reductive ring opening and utilizes two Baldwin-Lee CsF/cat. CuI Stille cross-coupling reactions with vinylstannanes 8 and 3 to efficiently elaborate the C(1) C(4) and C(14) C(18) sectors.

  DOI：

  10.1021/acs.orglett.5b01966
• 作为产物：
  描述：

  异丁酸乙酯 在 吡啶 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 48.58h， 生成 ethyl 2,2-dimethyl-3-(4-toluenesulfonyloxy)butanoate
  参考文献：
  名称：

  Total Synthesis of the Potent HIF-1 Inhibitory Antitumor Natural Product, (8R)-Mycothiazole, via Baldwin–Lee CsF/CuI sp³–sp²-Stille Cross-Coupling. Confirmation of the Crews Reassignment

  摘要：

  A convenient asymmetric total synthesis of the potent HIF-1 inhibitory antitumor natural product, (-)- or (+)-(8R)-mycothiazole (1), is described. Not only does our synthesis confirm the 2006 structural reassignment made by Crews (Crews, P., et al. J. Nat. Prod. 2006, 69, 145), it revises the [a]p data previously reported for this molecule in MeOH from -13.7 degrees to +42.3 degrees. The newly developed route to (8R)-1 sets the C(8)-OH stereocenter via Sharpless AE/2,3-epoxy alcohol reductive ring opening and utilizes two Baldwin-Lee CsF/cat. CuI Stille cross-coupling reactions with vinylstannanes 8 and 3 to efficiently elaborate the C(1) C(4) and C(14) C(18) sectors.

  DOI：

  10.1021/acs.orglett.5b01966

文献信息

• ANALOGS OF DEHYDROPHENYLAHISTINS AND THEIR THEAPEUTIC USE
  申请人：Palladino Michael A.

  公开号：US20080221122A1

  公开（公告）日：2008-09-11

  Compounds represented by the following structure (II) are disclosed: as are methods for making such compounds. Compositions and methods for treating various disease conditions including cancer and non-cancer diseases associated with vascular proliferation are also disclosed.

  由以下结构（II）表示的化合物已被披露：制备这种化合物的方法也已被披露。还披露了用于治疗各种疾病条件的组合物和方法，包括与血管增殖相关的癌症和非癌症疾病。
• Analogs of dehydrophenylahistins and their therapeutic use
  申请人：Palladino Michael

  公开号：US20070078138A1

  公开（公告）日：2007-04-05

  Compounds represented by the following structure (II) are disclosed: as are methods for making such compounds. Compositions and methods for treating various disease conditions including cancer and non-cancer diseases associated with vascular proliferation are also disclosed.

  本文揭示了由以下结构（II）所代表的化合物，以及制造这种化合物的方法。此外，还揭示了用于治疗各种疾病状况的组合物和方法，包括与血管增殖有关的癌症和非癌症疾病。
• ANALOGS OF DEHYDROPHENYLAHISTINS AND THEIR THERAPEUTIC USE
  申请人：Palladino Michael

  公开号：US20120277251A1

  公开（公告）日：2012-11-01

  Compounds represented by the following structure (II) are disclosed: as are methods for making such compounds. Compositions and methods for treating various disease conditions including cancer and non-cancer diseases associated with vascular proliferation are also disclosed.

  本文披露了以下结构（II）所代表的化合物，以及制备这些化合物的方法。此外，还披露了用于治疗各种疾病状况的组合物和方法，包括与血管增生相关的癌症和非癌性疾病。
• Total Synthesis of Anti-microtubule Diketopiperazine Derivatives:  Phenylahistin and Aurantiamine
  作者：Yoshio Hayashi、Sumie Orikasa、Koji Tanaka、Kaneo Kanoh、Yoshiaki Kiso

  DOI：10.1021/jo0012905

  日期：2000.12.1
• US7674903B2
  申请人：——

  公开号：US7674903B2

  公开（公告）日：2010-03-09