o-(S)-(2-methylbutoxy)phenyl bromide | 131759-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: o-(S)-(2-methylbutoxy)phenyl bromide
• 英文别名: 1-bromo-2-[(2S)-2-methylbutoxy]benzene
• CAS: 131759-35-8
• 化学式: C₁₁H₁₅BrO
• 分子量: 243.143
• InChiKey: FALQPWBUGGEKSP-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  o-(S)-(2-methylbutoxy)phenyl bromide 在 叔丁基锂 、 间氯过氧苯甲酸 作用下， 反应 7.67h， 生成 (-)-(2S,3R)-3--1,2-benzisothiazole 1,1-dioxide oxide
  参考文献：
  名称：

  Chemistry of oxaziridines. 15. Asymmetric oxidations using 3-substituted 1,2-benzisothiazole 1,1-dioxide oxides

  摘要：

  The synthesis and asymmetric oxidations of chiral nonracemic 3-substituted 1,2-benzisothiazole 1,1-dioxide oxides (6) are described. These new N-sulfonyloxaziridines are prepared by oxidation of the corresponding enantiomerically pure sulfonimines 5. These reagents oxidize sulfides to sulfoxides (11-52% ee), epoxidize nonfunctionalized alkenes (17-61% ee), and oxidize enolates to alpha-hydroxy carbonyl compounds (11-81% ee). Epoxidation of (-)-(S)-limonene with (+)-(2R,3S)-6a, a double asymmetric synthesis, affords a 93:7 cis/trans mixture of limonene oxides. Evaluation of possible transition-state structures suggests that the molecular recognition is primarily determined by steric factors. These reagents are less effective than N-sulfonyloxaziridines 1-3 in their asymmetric oxidations because they lack well-defined regions that are topologically dissimilar near the active site.

  DOI：

  10.1021/jo00002a056
• 作为产物：
  描述：

  S-(-)-2-甲基-1-丁醇 在 亚磷酸三苯酯 、 sodium hydroxide 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 13.33h， 生成 o-(S)-(2-methylbutoxy)phenyl bromide
  参考文献：
  名称：

  Chemistry of oxaziridines. 15. Asymmetric oxidations using 3-substituted 1,2-benzisothiazole 1,1-dioxide oxides

  摘要：

  The synthesis and asymmetric oxidations of chiral nonracemic 3-substituted 1,2-benzisothiazole 1,1-dioxide oxides (6) are described. These new N-sulfonyloxaziridines are prepared by oxidation of the corresponding enantiomerically pure sulfonimines 5. These reagents oxidize sulfides to sulfoxides (11-52% ee), epoxidize nonfunctionalized alkenes (17-61% ee), and oxidize enolates to alpha-hydroxy carbonyl compounds (11-81% ee). Epoxidation of (-)-(S)-limonene with (+)-(2R,3S)-6a, a double asymmetric synthesis, affords a 93:7 cis/trans mixture of limonene oxides. Evaluation of possible transition-state structures suggests that the molecular recognition is primarily determined by steric factors. These reagents are less effective than N-sulfonyloxaziridines 1-3 in their asymmetric oxidations because they lack well-defined regions that are topologically dissimilar near the active site.

  DOI：

  10.1021/jo00002a056

文献信息

• Chiral Molecular Propellers of Triarylborane Ammonia Adducts
  作者：Michael Kemper、Elric Engelage、Christian Merten

  DOI：10.1002/anie.202014130

  日期：2021.2.8

  boranes. For borane–amine adducts, such induced propeller chirality has not been reported yet due to the low energy barrier for racemization in common triarylboranes such as B(C6H5)3 or B(C6F5)3. Herein, we demonstrate that point chirality in side chains of chiral triarylborane–ammonia adducts, which feature intramolecular hydrogen bonds in addition to the dative N→B bond, can efficiently be transferred

  已将手性分子螺旋桨构象诱导为各种三芳基结构，包括三苯甲基衍生物和三芳基硼烷。对于硼烷-胺加合物，由于在常见的三芳基硼烷（如B（C 6 H 5）3或B（C 6 F 5）3）中外消旋的能量垒较低，因此尚未报道这种诱导的螺旋桨手性。在这里，我们证明手性三芳基硼烷-氨加合物的侧链中的点手性可以有效地转移到三芳基硼烷推进剂手性上，该分子具有分子内的氢键以及N→B键。利用X射线晶体学和ECD / VCD光谱进行结构表征，我们研究了三个结合了手性烷氧基侧基的空间要求不同的例子。我们阐明了分子螺旋桨的构象偏好。此外，我们表明，从分离的，仅隐含溶剂化的分子获得的计算预测的构象偏好实际上与实验观察到的相反。
• DAVIS, FRANKLIN;REDDY, R. THIMMA;MCCAULEY, JOHN P. (JR);PRZESLAWSKI, ROBE+, J. ORG. CHEM., 56,(1991) N, C. 809-815
  作者：DAVIS, FRANKLIN、REDDY, R. THIMMA、MCCAULEY, JOHN P. (JR)、PRZESLAWSKI, ROBE+

  DOI：——

  日期：——