(R)-2-(benzyloxy)-3-methylbutanal | 96925-01-8

• 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: (R)-2-(benzyloxy)-3-methylbutanal
• 英文别名: (R)-2-benzyloxy-3-methylbutanal；(2R)-3-methyl-2-phenylmethoxybutanal
• CAS: 96925-01-8；110840-39-6；149342-56-3；84994-60-5
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: VUURQDUGKXVUFO-LBPRGKRZSA-N

物化性质

• 沸点：
  256.9±15.0 °C(Predicted)
• 密度：
  0.997±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-(benzyloxy)-3-methylbutanal 在 咪唑 、 4-二甲氨基吡啶 、 ATNP 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 147.83h， 生成 methyl (2E,5S,6R)-6-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-7-methyloct-2-enoate
  参考文献：
  名称：

  使用新型路易斯酸铝三（2,6-二-2-萘基苯醚）进行不饱和酯和烯醇化醛的乙烯基羟醛反应

  摘要：

  描述了新型路易斯酸、三(2,6-二-2-萘基苯氧基铝) (ATNP) 的合成及其在巴豆酸甲酯和烯醇化醛之间的乙烯醇醛反应中的用途。ATNP 与 Yamamoto 的路易斯酸、三(2,6-二苯酚铝) (ATPH) 有关，但 2-萘基更有效地阻断醛的 α 位，从而在可烯醇化醛的存在下实现巴豆酸酯的选择性烯醇化. 然后，使用各种底物，乙烯基羟醛反应可以顺利进行并以高产率进行。

  DOI：

  10.1021/ol300738f
• 作为产物：
  描述：

  (R)-2-methyl-non-4-en-3-ol 在 二甲基硫 、 sodium hydride 、 臭氧 作用下， 生成 (R)-2-(benzyloxy)-3-methylbutanal
  参考文献：
  名称：

  Steric and Electronic Effects in Conformational Preferences of C1-Oxygenated Chiral Alkenes

  摘要：

  A variable temperature NMR study shows that the benzyl protective group on the hydroxy function of a chiral allylic alcohol enhances the CH eclipsed form (I). On the other hand, various silyl ethers enhance the preference for the CO eclipsed conformer. However, when both the allylic R group and the hydroxy protective group are bulky (R tert-butyl, P = TIPS), the staggered conformation of the chiral alkene becomes preferred. An acetate group does not have an apparent effect on the conformational preference of the protected allylic alcohol. These facts are explained in terms of steric and electronic interactions.

  DOI：

  10.1021/jo00112a012

文献信息

• Synthetic studies of didemnins. i. revision of the stereochemistry of the hydroxyisovalerylpropionyl (hip) unit.
  作者：William R. Ewing、Krishna L. Bhat、Madeleine M. Joullie

  DOI：10.1016/s0040-4020(01)96067-3

  日期：——

  Synthetic and spectral evidence for the absolute configuration of the asymmetric centers of the hydroxyisovalerylpropionyl (HIP) unit present in the depsipeptides didemnins is discussed.

  合成和光谱证据的绝对构型中存在于二肽双氢精蛋白中的羟基异戊二酰基丙酰基（HIP）单元的不对称中心。
• Access to Functionalized Steroid Side Chains via Modified Julia Olefination
  作者：Enver Cagri Izgu、Aaron C. Burns、Thomas R. Hoye

  DOI：10.1021/ol102936z

  日期：2011.2.18

  Various functionalized steroidal side chains were conveniently accessed by a modified Julia olefination strategy using a common sulfone donor and an appropriate α-branched aldehyde acceptor. For the coupling of these hindered classes of reaction partners (and in contrast to typically observed trends), the benzothiazolyl(BT)-sulfone anion gave superior outcomes compared to the phenyltetrazolyl(PT)-sulfone

  使用常见的砜供体和合适的α-支化醛受体，通过改进的 Julia 烯化策略可以方便地获得各种功能化的甾体侧链。对于这些受阻类别的反应伙伴的偶联（并且与通常观察到的趋势相反），与苯基四唑基 (PT)-砜阴离子相比，苯并噻唑基 (BT)-砜阴离子具有更好的结果。
• Synthesis of 26,27-bisnorcastasterone analogs and analysis of conformation–activity relationship for brassinolide-like activity
  作者：Shuji Yamamoto、Bunta Watanabe、Junko Otsuki、Yoshiaki Nakagawa、Miki Akamatsu、Hisahi Miyagawa

  DOI：10.1016/j.bmc.2005.10.024

  日期：2006.3

  Three castasterone (CS) derivatives with varied side-chain moieties, 26,27-bisnorcastasterone (20S-bisilorCS), 20-epi-26,27-bisnorcastastcrone (20R-bisnorCS), and 21,26,27-trisnorcastasterone (trisnorCS), were synthesized stereoselectively from either stigmasterol or dehydroisoandrosterone. The 50% effective doses (ED50, nmol/plant) in the concentration-response Curve for brassinolide-like activity in the rice lamina inclination assay were determined to be 0.020 nmol (pED(50) = 10.7) for 20S-bisnorCS, 3.2 nmol (pED50 = 8.5) for 20R-bisnorCS, and 2.0 nmol (pED50 = 8.7) for trisnorCS. An analog containing an ester linkage between the steroid and the side-chain moiety of 20S-bisnorCS was also synthesized and its activity was evaluated to be 3.2 nmol (pED50 = 8.5), being equipotent to 20R-bisnorCS and trisnorCS. The activity of 20S-bisnorCS was 1/40 that of CS. The conformation analysis was conducted using a systematic search, showing that the activity decreases with an increase in the degree of freedom of the side chain of the steroidal skeleton. (c) 2005 Elsevier Ltd. All rights reserved.
• KO, KWANG-YOUN;FRAZEE, W. J.;ELIEL, E. L., TETRAHEDRON, 1984, 40, N 8, 1333-1343
  作者：KO, KWANG-YOUN、FRAZEE, W. J.、ELIEL, E. L.

  DOI：——

  日期：——
• The Vinylogous Aldol Reaction of Unsaturated Esters and Enolizable Aldehydes Using the Novel Lewis Acid Aluminum Tris(2,6-di-2-naphthylphenoxide)
  作者：Jeffrey A. Gazaille、Tarek Sammakia

  DOI：10.1021/ol300738f

  日期：2012.6.1

  (ATNP), and its use in the vinylogous aldol reaction between methyl crotonate and enolizable aldehydes are described. ATNP is related to Yamamoto’s Lewis acid, aluminum tris(2,6-diphenylphenoxide) (ATPH), but the 2-naphthyl groups more effectively block the α-position of aldehydes, enabling the selective enolization of crotonate esters in the presence of enolizable aldehydes. Vinylogous aldol reactions

  描述了新型路易斯酸、三(2,6-二-2-萘基苯氧基铝) (ATNP) 的合成及其在巴豆酸甲酯和烯醇化醛之间的乙烯醇醛反应中的用途。ATNP 与 Yamamoto 的路易斯酸、三(2,6-二苯酚铝) (ATPH) 有关，但 2-萘基更有效地阻断醛的 α 位，从而在可烯醇化醛的存在下实现巴豆酸酯的选择性烯醇化. 然后，使用各种底物，乙烯基羟醛反应可以顺利进行并以高产率进行。