(S)-3-((tert-butyldimethylsilyl)oxy)-3-phenylpropanal | 412912-89-1

• 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: (S)-3-((tert-butyldimethylsilyl)oxy)-3-phenylpropanal
• 英文别名: (3S)-3-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanal
• CAS: 412912-89-1
• 化学式: C₁₅H₂₄O₂Si
• 分子量: 264.44
• InChiKey: NPDZMJZFCWNCRR-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  (S)-3-((tert-butyldimethylsilyl)oxy)-3-phenylpropanal 在 甲醇 、 对甲苯磺酸 作用下， 反应 1.0h， 生成 (S)-3-hydroxy-3-phenyl-propionaldehyde
  参考文献：
  名称：

  A flexible enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A using asymmetric transfer hydrogenation/tandem Grubbs cross-metathesis/oxy-Michael reaction as key steps

  摘要：

  An efficient enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A was achieved by the use of asymmetric transfer hydrogenation (ATH)/tandem Grubbs cross-metathesis/oxy-Michael reaction. Furthermore, this strategy allows for diastereodivergent access to every representative member of the family. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.01.005
• 作为产物：
  描述：

  (S)-1-苯基-3-丁烯-1-醇 在 咪唑 、 2,6-二甲基吡啶 、 sodium periodate 、 四氧化锇 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 (S)-3-((tert-butyldimethylsilyl)oxy)-3-phenylpropanal
  参考文献：
  名称：

  A Short and Efficient Synthesis of (-)-Diospongin A

  摘要：

  已从苯甲醛合成了（-）-迪奥斯庞金 A，历时六步，总体产率为29%。

  DOI：

  10.1055/s-2006-956485

文献信息

• A Designed Amide as an Aldol Donor in the Direct Catalytic Asymmetric Aldol Reaction
  作者：Karin Weidner、Naoya Kumagai、Masakatsu Shibasaki

  DOI：10.1002/anie.201403118

  日期：2014.6.10

  The direct catalytic asymmetric aldol reaction offers efficient access to β‐hydroxy carbonyl entities. Described is a robust direct catalytic asymmetric aldol reaction of α‐sulfanyl 7‐azaindolinylamide, thus affording both aromatic and aliphatic β‐hydroxy amides with high ee values. The design of this transformation features a cooperative interplay of a soft and a hard Lewis acid, which together facilitate

  直接催化不对称醛醇缩合反应可高效地获得β-羟基羰基实体。描述了α-硫烷基7-氮杂吲哚基酰胺的鲁棒的直接催化不对称醛醇缩合反应，从而提供了具有高ee 值的芳族和脂族β-羟基酰胺。这种转化的设计具有软和硬路易斯酸的协同作用，它们共同促进了硬布朗斯台德碱对具有挑战性的化学选择性烯醇化作用。
• Confinement-Controlled, Either <i>syn</i>- or <i>anti</i>-Selective Catalytic Asymmetric Mukaiyama Aldolizations of Propionaldehyde Enolsilanes
  作者：Tynchtyk Amatov、Nobuya Tsuji、Rajat Maji、Lucas Schreyer、Hui Zhou、Markus Leutzsch、Benjamin List

  DOI：10.1021/jacs.1c07447

  日期：2021.9.15

  Protected aldols (i.e., true aldols derived from aldehydes) with either syn- or anti- stereochemistry are versatile intermediates in many oligopropionate syntheses. Traditional stereoselective approaches to such aldols typically require several nonstrategic operations. Here we report two highly enantioselective and diastereoselective catalytic Mukaiyama aldol reactions of the TBS- or TES- enolsilanes

  具有顺式或反式立体化学的受保护醛醇（即来自醛的真正醛醇）是许多低聚丙酸酯合成中的通用中间体。这种醛醇的传统立体选择性方法通常需要几个非战略性操作。在这里，我们报告了丙醛的 TBS-或 TES-烯醇硅烷与芳香醛的两种高度对映选择性和非对映选择性催化 Mukaiyama 羟醛反应。我们的反应以催化剂控制的方式直接提供有价值的甲硅烷基保护的丙醛醛醇，无论是合成还是反异构体。我们已经确定了一种特权 IDPi 催化剂基序，该基序专为控制这些醛醇化反应而设计，具有出色的选择性。我们展示了 IDPi 催化剂内核中的单原子修饰，用CF 2 H 基团替换 CF 3基团，如何导致醛的对映面分化发生戏剧性的转变。这种显着效果的起源归因于通过 CF 2 H 基团的非常规 C-H 氢键使催化腔变紧。
• Stereoselective synthesis of (−)-diospongins A and B and their stereoisomers at C-5
  作者：Nobuyuki Kawai、Sudhir Mahadeo Hande、Jun'ichi Uenishi

  DOI：10.1016/j.tet.2007.06.081

  日期：2007.9

  Antiosteoporotic diarylheptanoids (−)-diospongins A (1) and B (2) were synthesized stereoselectively. The key steps in the synthesis include a stereospecific PdII-catalyzed cyclization of chiral 1,5,7-trihydroxy-2-heptenes, 6a and 6b, to form cis and trans tetrahydropyran rings and a regioselective Wacker oxidation of β-(tetrahydro-2H-pyran-2-yl)styrenes, 5a and 5b. Their C-5 epimers 3 and 4 were also

  立体选择性地合成了抗骨质疏松症的二芳基庚烷类化合物（-）-双鞘脂A（1）和B（2）。合成的关键步骤包括手性1,5,7-三羟基-2-庚烯6a和6b的立体定向Pd II催化环化反应，形成顺式和反式四氢吡喃环，以及β-（四氢- 2 H-吡喃-2-基）苯乙烯5a和5b。还合成了它们的C-5差向异构体3和4。
• A flexible enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A using asymmetric transfer hydrogenation/tandem Grubbs cross-metathesis/oxy-Michael reaction as key steps
  作者：Gullapalli Kumaraswamy、Dasa Rambabu

  DOI：10.1016/j.tetasy.2013.01.005

  日期：2013.2

  An efficient enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A was achieved by the use of asymmetric transfer hydrogenation (ATH)/tandem Grubbs cross-metathesis/oxy-Michael reaction. Furthermore, this strategy allows for diastereodivergent access to every representative member of the family. (C) 2013 Elsevier Ltd. All rights reserved.
• A Short and Efficient Synthesis of (-)-Diospongin A
  作者：Janine Cossy、Cyril Bressy、Florent Allais

  DOI：10.1055/s-2006-956485

  日期：2006.12

  The synthesis of (-)-diospongin A has been achieved from benzaldehyde in six steps with an overall yield of 29%.

  已从苯甲醛合成了（-）-迪奥斯庞金 A，历时六步，总体产率为29%。