(S)-4-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyraldehyde | 149180-87-0

• 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)-4-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyraldehyde
• CAS: 149180-87-0
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: YQTRTFZBIHJZQB-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-4-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyraldehyde 在 lithium aluminium tetrahydride 、 丙酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Ansa Macrolides as Molecular Workbenches: Stereocontrolledsyn Additions toE olefins

  摘要：

  Fixed on an aromatic platform in a conformationally defined way, acyclic (E)-alkenes can be considered gripped on a molecular workbench. The olefinic ansa-macrolides formed in this way are shielded on one face. On epoxidation and dihydroxylation [Eq. (1)] the attack on the double bond takes place diastereoselectively from outside the ring, and the ansa chain can subsequently be cleaved from the workbench by mild hydrogenolysis. Bn=benzyl, NMO=N-methylmorpholin-N-oxide.

  DOI：

  10.1002/(sici)1521-3773(19980619)37:11<1566::aid-anie1566>3.0.co;2-u
• 作为产物：
  描述：

  (S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-en-1-ol 在 咪唑 、 sodium hydride 、 臭氧 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-4-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyraldehyde
  参考文献：
  名称：

  Ansa Macrolides as Molecular Workbenches: Stereocontrolledsyn Additions toE olefins

  摘要：

  Fixed on an aromatic platform in a conformationally defined way, acyclic (E)-alkenes can be considered gripped on a molecular workbench. The olefinic ansa-macrolides formed in this way are shielded on one face. On epoxidation and dihydroxylation [Eq. (1)] the attack on the double bond takes place diastereoselectively from outside the ring, and the ansa chain can subsequently be cleaved from the workbench by mild hydrogenolysis. Bn=benzyl, NMO=N-methylmorpholin-N-oxide.

  DOI：

  10.1002/(sici)1521-3773(19980619)37:11<1566::aid-anie1566>3.0.co;2-u

文献信息

• Two-Carbon Chain Extension of Chiral Aldehydes via 2-Alkenylthiazoles: Synthesis of γ-Functionalized Alkanals
  作者：Alessandro Dondoni、Pedro Merino、Jesus Orduna、Daniela Perrone

  DOI：10.1055/s-1993-25844

  日期：——

  The reaction of 2-thiazolylmethylenetriphenylphosphorane (1a) in benzene with various aldehydes gives 2-alkenylthiazoles in variable E/Z ratios. Application of the thiazole-to-formyl deblocking protocol to the mixture of the olefins leads to saturated aldehyde homologues having two more carbon atoms.

  2-噻唑基亚甲基三苯基膦（1a）在苯中与各种醛发生反应，生成不同 E/Z 比的 2-烯基噻唑。在烯烃混合物中应用噻唑-甲酰基脱锁协议，可以得到多两个碳原子的饱和醛同系物。