monoisopinocampheylborane | 28875-08-3

• 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: monoisopinocampheylborane
• 英文别名: isopinocampheyl-borane；Monoisopinocamphenylboran；(2,6,6-Trimethyl-3-bicyclo[3.1.1]heptanyl)borane
• CAS: 28875-08-3
• 化学式: C₁₀H₁₉B
• mdl: MFCD24390194
• 分子量: 150.072
• InChiKey: ZFWNFCSCXODQSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  monoisopinocampheylborane 、 1-苯基环戊烯 在 甲醇 作用下， 生成 methyl trans-2-phenylcyclopentylisopinocampheylborinate
  参考文献：
  名称：

  通过有机硼烷的手性合成：XVI。衍生自α-氨基酸和硼酸酯或硼酸酯的硼恶唑烷酮。将硼酸盐和硼酸盐升级为高光学纯度的材料的简单程序

  摘要：

  探索了由硼酸酯和硼酸酯与α-氨基酸合成硼杂环的方法，该方法可提高非对称氢硼化中间体的光学纯度。B-甲氧基-9-硼环[3.3.1]壬烷，二环己基硼酸甲酯和（+）-和（-）-甲基二异樟脑基硼酸酯与各种α-氨基酸反应形成相应的结晶螯合物。从甲基产生的螯合物的重结晶的反式-2- phenylcyclopentylisopinocampheylborinate 85％ee的与升-苯丙氨酸，甲基isopinocampheyl-外-norbornylborinate用83％ee的的升-脯氨酸，并用92％ee的的甲基diisopinocampheylborinate的两个光学异构体升-脯氨酸可产生相应的光学纯度接近100％ee的产品。在用亚氨基二乙酸和N-甲基亚氨基二乙酸处理后，环戊基硼酸二甲酯，外-降冰片基硼酸二甲酯和异-异樟脑基硼酸二甲酯形成相应的双环硼酸酯。衍生自3-四氢吡喃基硼酸二乙酯和亚氨基二乙

  DOI：

  10.1016/0022-328x(88)89064-8
• 作为产物：
  描述：

  葑烯 生成 monoisopinocampheylborane
  参考文献：
  名称：

  SATTERWHITE, D. MICHAEL;CROTEAU, RODNEY B., J. CHROMATOGR., 407,(1987) 243-252

  摘要：

  DOI：
• 作为试剂：
  描述：

  3-methyl-1,1-diphenyl-silacyclopent-3-ene 在 monoisopinocampheylborane 、 双氧水 、 sodium hydroxide 作用下， 以86%的产率得到(3S,4S)-4-methyl-3-hydroxy-1,1-diphenylsilolane
  参考文献：
  名称：

  Serine Protease Inhibition by a Silanediol Peptidomimetic

  摘要：

  Silanediol peptidomimetics are demonstrated to inhibit a serine protease. Asymmetric synthesis of the inhibitor was accomplished using Brown hydroboration and CBS reduction of an acylsilane intermediate. The silanediol product was found to inhibit the serine protease chymotrypsin with a K-i of 107 nM. Inhibition of the enzyme may involve exchange of a silane hydroxyl with the active site serine nucleophile, contrasting with previous silanediol protease inhibitors.

  DOI：

  10.1021/ol301933n

文献信息

• Process and intermediates for preparation of substituted piperidines
  申请人：Hoffmann-La Roche Inc.

  公开号：US06274735B1

  公开（公告）日：2001-08-14

  The present invention concerns intermediates useful in and a process for the preparation of a compound of formula 1 or a salt thereof comprising a) hydroboration of a compound of formula 2 A, R1 and R2 are as herein defined. These compounds are useful in the synthesis of renin inhibitors.

  本发明涉及在制备化合物1或其盐的过程中有用的中间体和方法，包括a) 对化合物2进行氢硼化反应，其中A、R1和R2如本文所定义。这些化合物在合成肾素抑制剂中很有用。
• [EN] 7H-8,9-DIHYDRO-PYRANO (2,3-C) IMIDAZO (1,2A) PYRIDINE DERIVATIVES AND THEIR USE AS GASTRIC ACID SECRETION INHIBITORS<br/>[FR] IMIDAZOPYRIDINES TRICYCLIQUES
  申请人：ALTANA PHARMA AG

  公开号：WO2005090358A3

  公开（公告）日：2006-01-26
• Molecular Addition Compounds. 15. Synthesis, Hydroboration, and Reduction Studies of New, Highly Reactive <i>tert</i>-Butyldialkylamine−Borane Adducts
  作者：Herbert C. Brown、Josyula V. B. Kanth、Pramod V. Dalvi、Marek Zaidlewicz

  DOI：10.1021/jo990379b

  日期：1999.8.1

  Two series of tert-butyldialkylamines have been prepared and examined for borane complexation. The complexing ability of each amine in the two series examined decreases in the order shown. First series: t-BuN(CH2CH2)(2)O 1a > t-BuNEt2 Ib > t-BuNPr(2)(n)1c > t-BuN(CH2CH2OMe)(2) Id much greater than t-BuNBu2i le. Second series: t-(BuNBuMe)-Me-i 2a > t-(BuNPrMe)-Me-i 2b > t-(BuNBuEt)-Et-i 2c > t-(BuNBuPrn)-Pr-i 2d much greater than t-(BuNPrEt)-Et-i 2e. The reactivity of the corresponding borane adducts toward 1-octene increases in the reverse order. The following amines form highly reactive liquid borane adducts hydroborating 1-octene in tetrahydrofuran at room temperature in less than 1 h: t-BuN(CH2CH2OMe)(2), t-(BuNBuEt)-Et-i, and t-(BuNPrMe)-Me-i. The limit of borane complexation among the amines examined is reached for t-BuNBu2i exchanging borane neither with EMS nor with BH3-THF. Among the various borane adducts prepared, the more promising borane adducts, t-Bu(CH3OCH2CH2)(2)N-BH3 (7), t-(BuMePrN)-N-i-BH3 (8), and t-(BuEtBuN)-N-i-BH3 (9), were selected for complete hydroboration and reduction studies. Hydroboration studies with the new, highly reactive trialkylamine-borane adducts 7-9 and representative olefins, such as l-hexene, styrene, beta-pinene, cyclopentene, norbornene, cyclohexene, 2-methyl-2-butene, alpha-pinene, and 2,3-dimethyl-2-butene, in tetrahydrofuran, dioxane, tert-butyl methyl ether, n-pentane, and dichloromethane, at room temperature (22 +/- 3 degrees C) were carried out. The reactions are faster in dioxane, requiring 1-2 h for the hydroboration of simple, unhindered olefins to the trialkylborane stage. Moderately hindered olefins, such as cyclohexene and 2-methyl-2-butene, give the corresponding dialkylboranes rapidly, with further slow hydroboration. However, the more hindered olefins, alpha-pinene and 2,3-dimethyl-2-butene, give stable monoalkylboranes very rapidly, with further hydroboration proceeding relatively slowly. The hydroborations can also be carried out conveniently in other solvents, such as THF, tert-butyl methyl ether, and n-pentane. A significant; rate retardation is observed in dichloromethane. Regioselectivity studies of l-hexene and styrene using these amine-borane adducts show selectivities similar to that of BH3-THF. The rates and stoichiometry of the reaction of t-BuMePriN-BH3 in tetrahydrofuran with selected organic compounds containing representative functional groups were also examined at room temperature. The reductions of esters, amides, and nitriles, which exhibit a sluggish reaction at room temperature, proceed readily under reflux conditions in tetrahydrofuran and dioxane and without solvent (at 85-90 degrees C). The carrier amines can be recovered by simple acid-base manipulations in good yield and readily recycled to make the borane adducts.
• MANDAL A. K.; TADHAV P. K.; BRO H. C., J. ORG. CHEM., 1980, 45, NO 17, 3543-3544
  作者：MANDAL A. K.、 TADHAV P. K.、 BRO H. C.

  DOI：——

  日期：——
• SREBNIK, MORRIS;COLE, THOMAS E.;RAMACHANDRAN, P. VEERARAGHAVAN BROWN HERB+, J. ORG. CHEM., 54,(1989) N6, C. 6085-6096
  作者：SREBNIK, MORRIS、COLE, THOMAS E.、RAMACHANDRAN, P. VEERARAGHAVAN BROWN HERB+

  DOI：——

  日期：——