正丁基硼酸(1S,2S,3R,5S)-(+)-2,3-蒎烷二醇酯 | 85167-10-8

• 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
• 中文名称: 正丁基硼酸(1S,2S,3R,5S)-(+)-2,3-蒎烷二醇酯
• 中文别名: (1S,2S,3R,5S)-(+)-2,3-蒎烷二醇丁基硼酸酯；正丁基硼酸(1S,2S,3R,5S)-(+)-2,3-蒎烷二醇酯,95
• 英文名称: (s)-pinanediol butylboronate
• 英文别名: (3aS,4S,6S,7aR)-2-Butyl-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole；(1S,2S,6R,8S)-4-butyl-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane
• CAS: 85167-10-8
• 化学式: C₁₄H₂₅BO₂
• 分子量: 236.162
• InChiKey: IMUJPBOUZJFWJB-FMSGJZPZSA-N

物化性质

• 溶解度：
  乙醇、乙酸乙酯
• 稳定性/保质期：
  按规定使用和贮存的该物质不会分解，并应避开氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  17
• 可旋转键数：
  3
• 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

安全信息

• 储存条件：
  请将药品存放在密闭、阴凉、干燥的地方。

反应信息

• 作为反应物：
  描述：

  正丁基硼酸(1S,2S,3R,5S)-(+)-2,3-蒎烷二醇酯 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 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 二氯甲烷 为溶剂， 反应 52.0h， 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：

  正丁基硼酸 、 (1S,2S,3R,5S)-(+)-2,3-蒎烷二醇 以 乙醚 为溶剂， 反应 3.0h， 以98%的产率得到正丁基硼酸(1S,2S,3R,5S)-(+)-2,3-蒎烷二醇酯
  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

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
• Synthesis of Boronic Esters from Organometallic Reagents and Bis(pinacolato)diboron
  作者：Swagata Paul、Santanu Panda

  DOI：10.1002/asia.202300911

  日期：2024.2.16

  We have successfully synthesized alkyl, aryl, and vinyl boronic esters carrying various chiral and achiral diol-protecting groups starting from the corresponding alkyl, aryl, and vinyl lithium or Grignard reagents via lithiation borylation strategy using bis-boronic esters.

  我们已经成功地从相应的烷基、芳基和乙烯基锂或格氏试剂出发，通过使用双硼酸酯的锂化硼基化策略合成了带有各种手性和非手性二醇保护基团的烷基、芳基和乙烯基硼酸酯。
• 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：——
• Suzuki–Miyaura cross-coupling of lithium n-alkylborates
  作者：Gang Zou、J.R Falck

  DOI：10.1016/s0040-4039(01)01128-5

  日期：2001.8

  The palladium-catalyzed cross-coupling of lithium n-alkylborates, generated in situ via addition of see-butyl lithium to boronate esters, proceeds in moderate to good yields with a wide variety of electrophiles. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Asymmetric synthesis of alkylarylcarbinols via reaction of a chiral pinanediol alkylboronic ester with arylmethyl chlorides
  作者：George W. Kabalka、Nan-Sheng Li、Su Yu

  DOI：10.1016/s0957-4166(97)00565-x

  日期：1997.12

  The reaction of arylmethyl chlorides with chiral pinanediol esters of alkylboronic acids in the presence of lithium dicyclohexylamide affords chiral alkylarylcarbinols in good stereochemical yields after oxidation. (C) 1997 Elsevier Science Ltd. All rights reserved.