2-benzyl-3-hydroxypropyl 4-toluenesulfonate | 157318-66-6

• 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: 2-benzyl-3-hydroxypropyl 4-toluenesulfonate
• 英文别名: (2-Benzyl-3-hydroxypropyl) 4-methylbenzenesulfonate
• CAS: 157318-66-6
• 化学式: C₁₇H₂₀O₄S
• 分子量: 320.409
• InChiKey: MPRJQDRENSCHRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-benzyl-3-hydroxypropyl 4-toluenesulfonate 在 四丁基溴化铵 、 sodium bromide 作用下， 以 甲苯 为溶剂， 反应 144.0h， 以65%的产率得到2-benzyl-3-hydroxypropyl bromide
  参考文献：
  名称：

  Epoxidation of Peptidyl Olefin Isosteres. Stereochemical Induction Effect of Chiral Centers at Four Adjacent Cα Positions

  摘要：

  Four tripeptidyl olefin isosteres were prepared, each of which contains a single chiral center derived from the bulky amino acid phenylalanine at positions corresponding to the P-2-P'(2) positions of a protease substrate. The effect of these chiral centers on the stereochemical outcome of mCPBA epoxidation of the olefin functionality was studied. A chiral center at P-2 or P'(2) position has no significant effect, and the P'(1) position exerts a small stereoselectivity. A chiral center at the P-1 position, on the other hand, has a profound chiral induction effect on the epoxidation reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00036-3
• 作为产物：
  描述：

  苄基丙二酸二乙酯 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 24.0h， 生成 2-benzyl-3-hydroxypropyl 4-toluenesulfonate
  参考文献：
  名称：

  Novel peptide isosteres that were designed to inhibit the binding of the HIV surface glycoprotein (gp120) to the T cell surface glycoprotein CD4

  摘要：

  (2S)-2-[3′(RS)-3′-苄基-3′-苄氧羰基丙-1′-烯基]-N-甲氧羰基吡咯烷的顺式和反式异构体是由(S)-N-叔丁氧羰基脯氨醛和(2RS)-3-碘-2-苄基-1-三异丙基硅氧基丙烷的磷酰亚胺通过威蒂希反应制备的。此外，(2S)-N-甲氧基羰基-2-[(3′RS)-1-氧代-3′-苄基-3′-苄氧基羰基丙基]吡咯烷是由维蒂希反应生成的顺式烯制备的。这些肽本打算作为已知的艾滋病毒淋巴细胞结合抑制剂 N-甲氧基羰基羰基丙氨酰苯丙苄酯的肽等效物，但并不具有这种活性。

  DOI：

  10.1039/a800756j

文献信息

• Regioselective, Borinic Acid-Catalyzed Monoacylation, Sulfonylation and Alkylation of Diols and Carbohydrates: Expansion of Substrate Scope and Mechanistic Studies
  作者：Doris Lee、Caitlin L. Williamson、Lina Chan、Mark S. Taylor

  DOI：10.1021/ja302549c

  日期：2012.5.16

  regioselective monofunctionalization of 1,2- and 1,3-diols are presented. Diarylborinic acid catalysis is shown to be an efficient and general method for monotosylation of pyranoside derivatives bearing three secondary hydroxyl groups (7 examples, 88% average yield). In addition, the scope of the selective acylation, sulfonylation, and alkylation is extended to 1,2- and 1,3-diols not derived from carbohydrates

  介绍了二芳基硼酸催化的 1,2-和 1,3-二醇的区域选择性单官能化的合成和机械方面。二芳基硼酸催化被证明是对带有三个仲羟基的吡喃糖苷衍生物进行单甲苯基化的一种有效且通用的方法（7 个例子，平均产率 88%）。此外，选择性酰化、磺酰化和烷基化的范围扩展到非碳水化合物衍生的 1,2- 和 1,3- 二醇（28 个例子）；该方法的效率、通用性和操作简单性与包括广泛应用的有机锡催化或介导反应在内的最先进方案相比具有竞争力。使用竞争实验、动力学和催化剂结构-活性关系探索有机硼催化过程的机制细节。
• Novel peptide isosteres that were designed to inhibit the binding of the HIV surface glycoprotein (gp120) to the T cell surface glycoprotein CD4
  作者：Michael G. B. Drew、Stephen Gorsuch、John Mann、Shimon Yoshida

  DOI：10.1039/a800756j

  日期：——

  The cis- and trans-isomers of (2S)-2-[3′(RS)-3′-benzyl-3′-benzyloxycarbonylprop-1′-enyl]-N-methoxycarbonylcarbonylpyrrolidines have been prepared from a Wittig reaction between (S)-N-Boc-prolinal and the phosphorus ylide from (2RS)-3-iodo-2-benzyl-1-triisopropylsilyloxypropane. In addition, (2S)-N-methoxycarbonylcarbonyl-2-[(3′RS)-1-oxo-3′-benzyl-3′-benzyloxycarbonylpropyl]pyrrolidine was prepared from the cis-alkene produced in the Wittig reaction. These were intended as peptide isosteres of the known inhibitors of HIV-lymphocyte binding N-methoxycarbonylcarbonylprolylphenylalanyl benzyl esters, but did not possess such activity.

  (2S)-2-[3′(RS)-3′-苄基-3′-苄氧羰基丙-1′-烯基]-N-甲氧羰基吡咯烷的顺式和反式异构体是由(S)-N-叔丁氧羰基脯氨醛和(2RS)-3-碘-2-苄基-1-三异丙基硅氧基丙烷的磷酰亚胺通过威蒂希反应制备的。此外，(2S)-N-甲氧基羰基-2-[(3′RS)-1-氧代-3′-苄基-3′-苄氧基羰基丙基]吡咯烷是由维蒂希反应生成的顺式烯制备的。这些肽本打算作为已知的艾滋病毒淋巴细胞结合抑制剂 N-甲氧基羰基羰基丙氨酰苯丙苄酯的肽等效物，但并不具有这种活性。
• Conscripting the Active-Site Zinc Ion in Carboxypeptidase A in Inactivation Chemistry by a New Type of Irreversible Enzyme Inactivator
  作者：Yasuhiro Tanaka、Ioannis Grapsas、Srikanth Dakoji、Young June Cho、Shahriar Mobashery

  DOI：10.1021/ja00096a001

  日期：1994.8

  A new strategy for irreversible inactivation of the metalloenzyme carboxypeptidase A (CPA) involving a proposed activation of a carbon-iodide bond in an inactivator by the active-site zinc ion toward nucleophilic substitution is described. 2-Benzyl-3-iodopropanoic acid (compound 1) was designed to bind the active site of CPA. An energy-minimized complex of 1 in the active site of CPA reveals that the iodo moiety comes within the coordination sphere of the zinc ion. Such metal coordination was expected to facilitate the departure of the halide in an S(N)2-type reaction by the side-chain functions of either Glu-270 or Tyr-248. Compound 1 was shown-to inactivate CPA in a time-dependent manner, a process which was active-site directed and irreversible; a rate enhancement of approximately 10(8)-10(9)-fold is estimated for the inactivation chemistry by 1 over model metal-activated S(N)2 type reactions. 2-Benzyl-4-iodobutanoic acid (compound 6), an analog of 1 with an extended structure by one methylene unit, was shown to serve solely as a poor competitive inhibitor for CPA (K-i = 0.41 +/- 0.07 mM) but not as an irreversible inactivator; a discussion of the kinetic behavior by the two compounds is provided. The results reported herein hold the promise of a novel chemistry for selective inactivation of metalloenzymes.
• Epoxidation of Peptidyl Olefin Isosteres. Stereochemical Induction Effect of Chiral Centers at Four Adjacent Cα Positions
  作者：Nurit Perlman、Mordechai Livneh、Amnon Albeck

  DOI：10.1016/s0040-4020(00)00036-3

  日期：2000.3

  Four tripeptidyl olefin isosteres were prepared, each of which contains a single chiral center derived from the bulky amino acid phenylalanine at positions corresponding to the P-2-P'(2) positions of a protease substrate. The effect of these chiral centers on the stereochemical outcome of mCPBA epoxidation of the olefin functionality was studied. A chiral center at P-2 or P'(2) position has no significant effect, and the P'(1) position exerts a small stereoselectivity. A chiral center at the P-1 position, on the other hand, has a profound chiral induction effect on the epoxidation reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.