(s)-pinanediol (1S)-(1-chloropentyl)boronate | 85167-13-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (s)-pinanediol (1S)-(1-chloropentyl)boronate
• 英文别名: (S)-pinanediol (S)-1-(chloropentyl)boronate；(+)-pinanediol 1-chloro-pentyl-1-boronate；(1S,2S,6R,8S)-4-[(1S)-1-chloropentyl]-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane
• CAS: 85167-13-1
• 化学式: C₁₅H₂₆BClO₂
• 分子量: 284.634
• InChiKey: FBGKVFQZFAMHEM-WHPHWUKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (s)-pinanediol (1S)-(1-chloropentyl)boronate 在 N-甲基吗啉 、 盐酸 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 34.0h， 生成
  参考文献：
  名称：

  Boro-norleucine as a P1 residue for the design of selective and potent DPP7 inhibitors

  摘要：

  Dipeptide-based inhibitors with C-substituted (alkyl or aminoalkyl) alpha-amino acids in the P2 position and born-norleucine (boro-Nle) in the P1 position were synthesized. Relative to born-proline, boro-Nle as a P1 residue was shown able to significantly dial out DPP4, FAP, DPP8, and DPP9 activity. Dab-boro-Nle (4g) proved to be the most selective and potent DPP7 inhibitor with a DPP7 IC50 value of 480 pM. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.076
• 作为产物：
  描述：

  (S)-(1-chloropentyl)dichloroborane 以 甲醇 为溶剂， 生成 (s)-pinanediol (1S)-(1-chloropentyl)boronate
  参考文献：
  名称：

  在配位溶剂中用四氯硅烷将三氟硼酸烷基酯转化为烷基二氯硼烷。

  摘要：

  DOI：

  10.1002/anie.200453690

文献信息

• 99% Chirally selective synthesis via pinanediol boronic esters: insect pheromones, diols, and an amino alcohol
  作者：Donald S. Matteson、Kizhakethil Mathew. Sadhu、Mark L. Peterson

  DOI：10.1021/ja00264a039

  日期：1986.2

  Synthese en particulier du methyl-4 heptanol-3, brevicomine, eldanolide, decanediol-5,6, methyl-6 undecanediol-5,7 et amino-6 decanol-5

  合成这些特别是甲基-4 庚醇-3、短苯胺、eldanolide、癸二醇-5,6、甲基-6 十一烷二醇-5,7 和氨基-6 癸醇-5
• Stereospecific and Regioselective Synthesis of <i>E</i>-Allylic Alcohols through Reductive Cross Coupling of Terminal Alkynes
  作者：Austin B. Shaff、Langxuan Yang、Mitchell T. Lee、Gojko Lalic

  DOI：10.1021/jacs.3c06963

  日期：——

  convergent method for the synthesis of allylic alcohols that involves a reductive coupling of terminal alkynes with α-chloro boronic esters. The new method affords allylic alcohols with excellent regioselectivity (anti-Markovnikov) and an E/Z ratio greater than 200:1. The reaction can be performed in the presence of a wide range of functional groups and has a substrate scope that complements the stoichiometric

  我们开发了一种合成烯丙醇的收敛方法，涉及末端炔烃与 α-氯硼酸酯的还原偶联。新方法提供了具有优异区域选择性（抗马尔可夫尼科夫）和大于 200:1 的 E/Z 比的烯丙醇。该反应可以在多种官能团存在下进行，并且底物范围可补充使用烯基锂和格氏试剂进行的 α-氯硼酸酯的化学计量烯基化。该转化是立体定向的，可以稳健且高度选择性地合成手性烯丙醇。我们的研究支持涉及炔烃氢化以及烯基铜中间体与α-氯硼酸酯交叉偶联的机制。实验证据排除了交叉偶联步骤的根本机制，并且与硼酸盐中间体的形成和1,2-金属化物转变一致。
• Matteson, Donald S.; Ray, Rahul; Rocks, Richard R., Organometallics, 1983, vol. 2, # 11, p. 1536 - 1540
  作者：Matteson, Donald S.、Ray, Rahul、Rocks, Richard R.、Tsai, David J.

  DOI：——

  日期：——
• Design, Synthesis, Biological Evaluation, and Structure−Activity Relationship (SAR) Discussion of Dipeptidyl Boronate Proteasome Inhibitors, Part I: Comprehensive Understanding of the SAR of α-Amino Acid Boronates
  作者：Yongqiang Zhu、Xin Zhao、Xinrong Zhu、Gang Wu、Yuejie Li、Yuheng Ma、Yunxia Yuan、Jie Yang、Yang Hu、Li Ai、Qingzhi Gao

  DOI：10.1021/jm9005093

  日期：2009.7.23

  New series of dipeptidyl boronate inhibitors of 20S proteasome were designed and synthesized, The comprehensive understanding or the SAR was obtained by utilizing the variation of four substituents. From the screened compounds in enzyme, novel inhibitors 49 and 50 were identified to be highly potent druglike candidates with IC50 values of 1.2 and 1.6 nM, respectively, which showed better activities than the drug bortezomib on the market. Two hematologic human tumor cell lines, HL-60 and U266, were significantly sensitive to both candidates and showed nearly the same potency as the standard bortezomib with IC50 values less than 10 nM. But as for most of the eight human solid tumor cell lines, both candidates were more potent than the standard with the IC50 value range of 9.8-70 nM. The activity evaluation of the stereoisomers showed that changing R-isomers to S-isomers greatly reduced the potency and even induced inactivity.
• Diastereoselection in reactions of pinanediol dichloromethaneboronate
  作者：David J. S. Tsai、Pradipta K. Jesthi、Donald S. Matteson

  DOI：10.1021/om50005a010

  日期：1983.11