(1S,2S)-1-(3,5-dimethoxyphenyl)-1,2-propanediol | 207679-10-5

• 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: (1S,2S)-1-(3,5-dimethoxyphenyl)-1,2-propanediol
• CAS: 207679-10-5
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: PWGOLAOJILODQR-WRWORJQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  15.0
• 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：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,2S)-1-(3,5-dimethoxyphenyl)-1,2-propanediol 在 咪唑 、 盐酸 、 偶氮二异丁腈 、 叠氮磷酸二苯酯 、 四丁基氟化铵 、 水 、 三正丁基氢锡 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 5-[2-((R)-2-Azido-propyl)-4,6-dimethoxy-phenyl]-8-benzyloxy-1-methoxy-3-methyl-naphthalene
  参考文献：
  名称：

  Stereoselective synthesis of O,O-dimethylkorupensamine A via palladium(0)-mediated cross-coupling of a planar chiral (arene)Cr(CO)3 complex with naphthylboronic acid

  摘要：

  通过钯（0）介导的具有对映体纯度的三羰基铬络合物（3,5-dimethoxy-2-bromobenzene complex of 3,5-dimethoxy-2-bromobenzene having a functional group at C-1 position）与萘硼酸的交叉耦合，以萘硼酸为关键步骤立体选择性地合成了 O,O-二甲基こorupensamine A。

  DOI：

  10.1039/a800075a
• 作为产物：
  描述：

  (E)-1,3-dimethoxy-5-(prop-1-en-1-yl)benzene 在 AD-mix-α 、 甲基磺酰胺 、 水 作用下， 以 叔丁醇 为溶剂， 以99%的产率得到(1S,2S)-1-(3,5-dimethoxyphenyl)-1,2-propanediol
  参考文献：
  名称：

  Stereoselective synthesis of O,O-dimethylkorupensamine A via palladium(0)-mediated cross-coupling of a planar chiral (arene)Cr(CO)3 complex with naphthylboronic acid

  摘要：

  通过钯（0）介导的具有对映体纯度的三羰基铬络合物（3,5-dimethoxy-2-bromobenzene complex of 3,5-dimethoxy-2-bromobenzene having a functional group at C-1 position）与萘硼酸的交叉耦合，以萘硼酸为关键步骤立体选择性地合成了 O,O-二甲基こorupensamine A。

  DOI：

  10.1039/a800075a

文献信息

• Stereoselective synthesis of O,O-dimethylkorupensamine A via palladium(0)-mediated cross-coupling of a planar chiral (arene)Cr(CO)3 complex with naphthylboronic acid
  作者：Takashi Watanabe、Motokazu Uemura

  DOI：10.1039/a800075a

  日期：——

  O,O-Dimethylkorupensamine A was stereoselectively synthesized by using the palladium(0)-mediated cross-coupling of the enantiomerically pure tricarbonylchromium complex of 3,5-dimethoxy-2-bromobenzene having a functional group at C-1 position with naphthylboronic acid as a key step.

  通过钯（0）介导的具有对映体纯度的三羰基铬络合物（3,5-dimethoxy-2-bromobenzene complex of 3,5-dimethoxy-2-bromobenzene having a functional group at C-1 position）与萘硼酸的交叉耦合，以萘硼酸为关键步骤立体选择性地合成了 O,O-二甲基こorupensamine A。
• Stereoselective isomerisations of 4-(3′,5′-dimethoxyphenyl)-2,5-dimethyl-1,3-dioxolanes. Temperature-dependent formation of either isochromanes or dihydroisobenzofurans
  作者：Robin G. F. Giles、Rodney W. Rickards、Badra S. Senanayake

  DOI：10.1039/p19960002241

  日期：——

  Stereoselective isomerisation of rel-(2R,4S,5R)-4-(3',5'-dimethoxyphenyl)-2,5-dimethyl-1,3-dioxolane 7 with titanium tetrachloride affords rel-(1R,3R,4S)-4-hydroxy-6,8-dimethoxy-1,3-dimethylisochromane 19 and its C-1 epimer 20 in high yield, The former predominates at a reaction temperature of -78 degrees C and the latter at -30 degrees C, Similar isomerisation of the 1:1 mixture of rel-(2S,4R,5R)- and rel-(2R,4R,5R)-4-(3',5'-dimethoxyphenyl)-2,5-dimethyl- 1,3-dioxolanes 8 and 9 gives rel-(1R,3R,4R)-4-hydroxy-6,8-dimethoxy-1,3-dimethylisochromane 29 and its C-1 epimer 31, with the latter predominating at both -78 and -30 degrees C. At 0 degrees C, dioxolane 7 is isomerised to re[-(1S,1'R,3R)-1-(1'-hydroxyethyl)4,6-dimethoxy-3-methyl- 1,3-dihydroisobenzofuran 25 and its C-3 epimer 26 as the sole reaction products in a 10:1 ratio, Dioxolanes 8 and 9 are similarly converted into rel-(1R,1'R,3S)-1-(1'-hydroxyethyl)-4,6-dimethoxy-3-methyl-1,3-dihydroisobenzofuran 32 and its C-3 epimer 33, These furans probably arise through further isomerisation of the intermediate isochromanes at the higher reaction temperatures.
• Stereoselective Synthesis of Axially Chiral Natural Products, (−)-Steganone and O,O′-Dimethylkorupensamine A, Utilizing Planar Chiral (Arene)chromium Complexes
  作者：Ken Kamikawa、Takashi Watanabe、Akira Daimon、Motokazu Uemura

  DOI：10.1016/s0040-4020(99)01115-1

  日期：2000.4

  substituent of arylboronic acids and reaction conditions. The cross-coupling with o-alkyl or hydroxymethyl substituted arylboronic acids gave kinetically controlled products in which the ortho substituents were oriented in syn-configuration to the tricarbonylchromium fragment. On the other hand, o-formyl phenylboronic acid produced thermodynamically stable anti-coupling products under the same conditions

  钯（0）介导的碳酸钠存在下，在甲醇水溶液中回流下，平面手性（2,6-二取代溴苯）铬配合物与邻取代芳基硼酸的平面手性（2,6-二取代溴苯）铬络合物的Suzuki-Miyaura交叉偶联产生立体选择性的轴向手性单Cr（CO ）3层-complexed的联芳基。发现交叉偶联产物的轴向立体化学很大程度上取决于芳基硼酸的邻取代基的空间体积和反应条件。与邻烷基或羟甲基取代的芳基硼酸的交叉偶联产生动力学控制的产物，其中邻位取代基在顺式中取向-对三羰基铬片段的构型。另一方面，邻甲酰基苯基硼酸在相同条件下产生热力学稳定的抗偶联产物。通过利用这些方法的，生物活性轴向手性天然产物，（ - ） - steganone和ø，ö ' -二甲基衍生物korupensamine A的天然产物的，被立体选择性合成。