(2R,3S,4S)-2,4-dimethyl-1-phenylmethoxyhex-5-en-3-ol | 73814-78-5

• 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: (2R,3S,4S)-2,4-dimethyl-1-phenylmethoxyhex-5-en-3-ol
• CAS: 73814-78-5；85880-73-5
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: FMIOZEPTHKKAAN-GUTXKFCHSA-N

物化性质

• 沸点：
  348.8±30.0 °C(Predicted)
• 密度：
  0.985±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-2,4-dimethyl-1-phenylmethoxyhex-5-en-3-ol 在 咪唑 、 臭氧 、 溶剂黄146 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 122.0h， 生成 (2S,3S,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentanal
  参考文献：
  名称：

  A total synthesis of (.+-.)-tirandamycin B

  摘要：

  The total synthesis of the dienoyl tetramic acid antibiotic (+/-)-tirandamycin B is described. The key transformations of the strategy include (1) cyclization of pyranone 14 with fluorosilicic acid to provide the 2,6-dioxabicyclo[3.3.1]nonane system of the natural product, (2) reductive removal of the benzyl ether from enone 15, and (3) attachment of the tetramic acid moiety by using the Schlessinger phosphonate protocol. Protection of the primary hydroxyl function of tirandamycin B as the triisopropylsilyl (TIPS) ether was crucial to the success of the strategy.

  DOI：

  10.1021/ja00023a029
• 作为产物：
  描述：

  Toluene-4-sulfonic acid (2R,3R,4R)-5-benzyloxy-3-hydroxy-4-methyl-2-vinyl-pentyl ester 以92%的产率得到
  参考文献：
  名称：

  EVANS D. A.; SJOGREN E. B.; BARTROLI J.; DOW R. L., TETRAHEDRON LETT., 27,(1986) N 41, 4957-4960

  摘要：

  DOI：

文献信息

• Total synthesis of the polyether antibiotic ionomycin
  作者：David A. Evans、Robert L. Dow、Thomas L. Shih、James M. Takacs、Robert Zahler

  DOI：10.1021/ja00169a042

  日期：1990.6

  A convergent asymmetric synthesis of the calcium ionophore ionomycin has been achieved through a route that is outlined below. The four illustrated subunits, which comprise the c,-C,,-,, CI)-&r cI&22, and C=-C32 portions of ionomycin,

  钙离子载体离子霉素的会聚不对称合成已通过以下概述的途径实现。四个图示的亚基，它们包含离子霉素的 c,-C,,-,, CI)-&r cI&22 和 C=-C32 部分，
• An expeditious total synthesis of kalkitoxins: determination of the absolute stereostructure of natural kalkitoxin
  作者：Fumiaki Yokokawa、Toshinobu Asano、Tatsufumi Okino、William H. Gerwick、Takayuki Shioiri

  DOI：10.1016/j.tet.2004.06.014

  日期：2004.8

  Kalkitoxin, a potent neurotoxin isolated from the marine cyanobacteria Lyngbya majuscula, and its congeners (1–7) were efficiently synthesized utilizing Hruby's diastereoselective 1,4-addition and the Wipf's oxazoline-thiazoline conversion as key steps. These synthetic efforts in combination with spectral studies of natural kalkitoxin clearly determined the absolute stereostructure of kalkitoxin to

  Kalkitoxin，一种强效神经毒素从海洋蓝细菌分离鞘丝藻majuscula，其同类物（1 - 7）被有效地合成利用Hruby的非对映选择性1,4-加成和Wipf的恶唑啉噻唑啉转化为关键步骤。这些合成的努力与自然kalkitoxin的光谱研究相结合，明确确定kalkitoxin的绝对立体结构为7。
• Hydroformylation as a simple and efficient one carbon homologation of homoallylic alcohols. Synthesis of prelog-djerassi lactone.
  作者：P.G.M. Wuts、M.L. Obrzut、P.A. Thompson

  DOI：10.1016/s0040-4039(01)90179-0

  日期：1984.1

  A hydroformylation oxidation sequence is described for the efficient conversion of homoallylic alcohols to δ-lactones. The methodology is applied to the synthesis of Prelog-Djerassi lactone.

  描述了加氢甲酰化氧化顺序，用于将均烯丙基醇有效转化为δ-内酯。该方法应用于Prelog-Djerassi内酯的合成。
• Effects of Olefin Geometry on the Stereochemistry of Lewis Acid Mediated Additions of Crotylstannanes to Aldehydes
  作者：Gary E. Keck、Kenneth A. Savin、Erik N. K. Cressman、Duane E. Abbott

  DOI：10.1021/jo00104a054

  日期：1994.12

  The role of the double bond geometry (E/Z stereochemistry) in reactions of crotylstannanes with aldehydes has been examined for representative ''simple'', alpha-alkoxy, and beta-alkoxy aldehydes. For the reaction of crotylstannane with simple achiral aliphatic, aromatic, or alpha,beta unsaturated aldehydes mediated by BF3.Et(2)O, use of the E crotylstannane gives much enhanced syn selectivity over that obtained with Z (e.g., 43:1 vs 4:1 with benzaldehyde). A synclinal transition state in which the CH(2)SnBu(3) group is gauche to oxygen is proposed to explain these results. For alpha-alkoxy aldehydes, use of the E stannane with MgBr2 gives the highest syn selectivity, while the Z stannane gives slightly better stereoselectivity with beta-alkoxy substrates. In contrast, the use of TiCl4 gives anti products preferentially from the E stannane and either alpha or beta-alkoxy substrates.
• Crotylzirconium derivatives as a new reagent for the threo selective synthesis of β-methylhomoallyl alcohols
  作者：Yoshinori Yamamoto、Kazuhiro Maruyama

  DOI：10.1016/s0040-4039(01)81780-9

  日期：1981.1