(1R,2R)-2-amino-3-methoxy-1-phenylpropan-1-ol | 51594-35-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1R,2R)-2-amino-3-methoxy-1-phenylpropan-1-ol
• CAS: 51594-35-5
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: SNTCCWUWWYWRLN-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxy-1-naphthamide 、 (1R,2R)-2-amino-3-methoxy-1-phenylpropan-1-ol 在 triethyloxonium fluoroborate 作用下， 生成 (4R,5R)-4-(methoxymethyl)-2-(5-methoxynaphthalen-1-yl)-5-phenyl-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  Asymmetric additions to chiral naphthalenes. 4. Asymmetric synthesis of the AB-ring of aklavinone

  摘要：

  DOI：

  10.1021/jo00229a028
• 作为产物：
  描述：

  (4R,5R)-4-methoxymethyl-5-phenyl-1,3-oxazolidin-2-one 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 72.0h， 以50%的产率得到(1R,2R)-2-amino-3-methoxy-1-phenylpropan-1-ol
  参考文献：
  名称：

  胺的羧基化和Mitsunobu反应生成氨基甲酸酯：构型的保留与反转是取代基依赖性的。

  摘要：

  一种由氨基醇合成氨基甲酸酯的温和方法涉及与二氧化碳的顺序羧化，然后进行Mitsunobu反应。出乎意料的是，Mitsunobu反应的立体化学过程取决于氨基甲酸中间体是被氢（保留）还是被碳（转化）N-取代。

  DOI：

  10.1021/ol0491080

文献信息

• Method for preparation of sulphostin and its analogue or intermediates thereof
  申请人：Nagai Masashi

  公开号：US20050020834A1

  公开（公告）日：2005-01-27

  A method for preparing a compound represented by the following general formula (5) where, n is an integer of 0 to 3; and Y represents a protecting group for an amino group, the method including the steps of reacting a compound represented by the following general formula (3) where n and Y are as described above, with a silylating agent, and subsequently reacting it with P (═O) T 3 , where T represents a halogen atom, and further with ammonia. A method for preparing an optically active intermediate of sulphostin or an analogue thereof, which is an optically active amine salt of an optically active compound represented by the following general formula (8) where n is an integer of 0 to 3; Y represents a protecting group for the amino group; and each configuration at C* and P* may be the same or different and indicates S or R, the method including reacting a compound represented by the following general formula (7) where n and Y are as described above; and the configuration of C* indicates either of S or R, with an optically active amine, and resolving the formed diastereomeric salt by fractional crystallization.

  以下是一个制备以下通用式（5）所表示的化合物的方法，其中n为0到3的整数；Y表示氨基保护基。该方法包括以下步骤：将以下通用式（3）所表示的化合物与硅基化试剂反应，然后再与P（═O）T3（其中T表示卤素原子）反应，最后再与氨反应。 以下是制备sulphostin或其类似物的光学活性中间体的方法，该中间体是以下通用式（8）所表示的光学活性化合物的光学活性胺盐，其中n为0到3的整数；Y表示氨基保护基；C*和P*的每个构型可以相同也可以不同，并表示S或R。该方法包括将以下通用式（7）所表示的化合物与光学活性胺反应，并通过分数结晶分离形成的对映异构体盐。
• PROCESSES FOR PREPARATION OF SULPHOSTIN AND ITS ANALOGUES OR INTERMEDIATES THEREOF
  申请人：Nippon Kayaku Kabushiki Kaisha

  公开号：EP1457494A1

  公开（公告）日：2004-09-15

  A method for preparing a compound represented by the following general formula (5)    where, n is an integer of 0 to 3; and Y represents a protecting group for an amino group, the method including the steps of reacting a compound represented by the following general formula (3)    where n and Y are as described above, with a silylating agent, and subsequently reacting it with P (=O) T3, where T represents a halogen atom, and further with ammonia. A method for preparing an optically active intermediate of sulphostin or an analogue thereof, which is an optically active amine salt of an optically active compound represented by the following general formula (8) where n is an integer of 0 to 3; Y represents a protecting group for the amino group; and each configuration at C* and P* may be the same or different and indicates S or R, the method including reacting a compound represented by the following general formula (7) where n and Y are as described above; and the configuration of C* indicates either of S or R, with an optically active amine, and resolving the formed diastereomeric salt by fractional crystallization.

  一种制备由以下通式(5)代表的化合物的方法 其中，n 是 0 至 3 的整数；Y 代表氨基的保护基团，该方法包括以下步骤：使下一通式（3）所代表的化合物与硅烷化剂反应，其中 n 和 Y 如上所述。 其中，n 和 Y 如上所述，与硅烷化剂反应，然后与 P (=O) T3 反应，其中 T 代表卤素原子，再与氨反应。 一种制备舒磷定或其类似物的光学活性中间体的方法，该光学活性中间体是由下 列通式（8）代表的光学活性化合物的光学活性胺盐 其中 n 是 0 至 3 的整数；Y 代表氨基的保护基团；C* 和 P* 的每个构型可以相同或不同，并表示 S 或 R，该方法包括使下式通式（7）所代表的化合物反应 其中 n 和 Y 如上所述；C* 的构型表示 S 或 R，与光学活性胺反应，并通过分馏结晶分 解所形成的非对映异构盐。
• Nickel/Bis(oxazoline)-Catalyzed Asymmetric Negishi Arylations of Racemic Secondary Benzylic Electrophiles to Generate Enantioenriched 1,1-Diarylalkanes
  作者：Hien-Quang Do、E. R. R. Chandrashekar、Gregory C. Fu

  DOI：10.1021/ja408561b

  日期：2013.11.6

  A tertiary stereogenic center that bears two different aryl substituents is found in a variety of bioactive compounds, including medicines such as Zoloft and Detrol. We have developed an efficient method for the synthesis of enantioenriched 1,1-diarylalkanes from readily available racemic benzylic alcohols. Formation of a benzylic mesylate (which is not isolated), followed by treatment with an arylzinc reagent, LiI, and a chiral nickel/bis(oxazoline) catalyst, furnishes the Negishi cross-coupling product in high ee and good yield. A wide array of functional groups (e.g., an aryl iodide, a thiophene, and an N-Boc-indole) are compatible with the mild reaction conditions. This method has been applied to a gram-scale synthesis of a precursor to Zoloft.
• KAWAGUCHI, MAMORU;OHASHI, JUNICHI;KAWAKAMI, YUKIO;YAMAMOTO, YUKIO;ODA, JU+, SYNTHESIS, BRD, 1985, N 6-7, 701-703
  作者：KAWAGUCHI, MAMORU、OHASHI, JUNICHI、KAWAKAMI, YUKIO、YAMAMOTO, YUKIO、ODA, JU+

  DOI：——

  日期：——
• MEYERS, A. I.;HIGASHIYAMA, KIMIO, J. ORG. CHEM., 52,(1987) N 20, 4592-4597
  作者：MEYERS, A. I.、HIGASHIYAMA, KIMIO

  DOI：——

  日期：——