9H-fluoren-9-ylmethyl N-[(1R)-1-isocyanato-2-methylpropyl]carbamate | 611198-17-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9H-fluoren-9-ylmethyl N-[(1R)-1-isocyanato-2-methylpropyl]carbamate
• CAS: 611198-17-5
• 化学式: C₂₀H₂₀N₂O₃
• 分子量: 336.39
• InChiKey: NBLYOUCUODNOCT-IBGZPJMESA-N

物化性质

• 熔点：
  154 °C
• 沸点：
  496.1±28.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9H-fluoren-9-ylmethyl N-[(1R)-1-isocyanato-2-methylpropyl]carbamate 在 4-二甲氨基吡啶 、 甲酸 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到Fmoc-gVal-CO-H
  参考文献：
  名称：

  An Efficient Conversion of the Carboxylic Group of N-Fmoc α-Amino Acids/Peptide Acids into N-Formamides Employing Isocyanates as Key Intermediates

  摘要：

  [Graphics]Reaction of 96% formic acid with isocyanates derived from N-Fmoc alpha-amino acids/peptide acids catalyzed by DMAP has yielded a new class of stable formamides as crystalline solids which have been characterized by IR, H-1 NMR, C-13 NMR, and mass spectroscopy. Conversion of the side chain carboxylic acid of N-Fmoc-5-oxazolidinones of Asp/Glu into the N-formyl group also has been accomplished. The reaction is simple, mild, and high yielding.

  DOI：

  10.1021/jo701371k
• 作为产物：
  描述：

  9-芴甲醇 在 N-甲基吗啉 、 吡啶 、 sodium azide 、 sodium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 0.83h， 生成 9H-fluoren-9-ylmethyl N-[(1R)-1-isocyanato-2-methylpropyl]carbamate
  参考文献：
  名称：

  从5H-噻唑-4-酮和硝基烯烃催化合成对叔硫醇：双官能基于脲肽的布朗斯台德碱催化

  摘要：

  满载：基于脲肽的双官能布朗斯台德碱1有效促进α-巯基羧酸盐替代物与硝基烯烃的第一个直接催化迈克尔反应，该反应涉及完全取代的α-碳原子结构。

  DOI：

  10.1002/anie.201305644

文献信息

• Synthesis of Optically Active 2-Amino-1,3,4-oxadiazoles and their Hybrid Peptides
  作者：Chilakapati Madhu、Girish Prabhu、Rumpa Pal、T. N. Guru Row、Vommina V. Sureshbabu

  DOI：10.1002/jhet.2166

  日期：2015.9

  Synthesis of 2‐amino‐1,3,4‐oxadiazole derivatives of Nα‐Cbz(benzyloxycarbonyl)/Boc‐protected amino/peptide acids under sonication is described. The conditions involved in the present protocol are simple, mild, and racemization free. The utility of 2‐amino group in the substituted oxadiazoles for the incorporation of peptide and ureido bonds to obtain hybrid peptidomimetics is also delineated. The 2‐amino‐1

  的2-氨基-1,3,4-恶二唑衍生物的合成Ñ α -Cbz（苄氧羰基）/ Boc-保护的氨基/肽下超声处理的酸进行说明。本协议中涉及的条件是简单，温和的，无外消旋的。还描述了2-氨基在取代的恶二唑中用于掺入肽和脲基键以获得杂合拟肽的效用。2-氨基-1,3,4-恶二唑3b是单晶，其分子结构已通过X射线晶体学研究证实。
• Ureidopeptide‐Based Brønsted Bases: Design, Synthesis and Application to the Catalytic Enantioselective Synthesis of β‐Amino Nitriles from (Arylsulfonyl)acetonitriles
  作者：Saioa Diosdado、Rosa López、Claudio Palomo

  DOI：10.1002/chem.201304877

  日期：2014.5.19

  preparation of β‐amino nitriles. We present a highly efficient organocatalytic methodology for the stereoselective synthesis of β‐amino nitriles, in which the key to success is the use of ureidopeptide‐based Brønsted base catalysts in combination with (arylsulfonyl)acetonitriles as synthetic equivalents of the acetonitrile anion. The method gives access to a variety of β‐amino nitriles with good yields

  在亚胺上添加氰基烷基部分是制备β-氨基腈的一种非常有吸引力的方法。我们为立体选择性合成β-氨基腈提供了一种高效的有机催化方法，其中成功的关键是将基于尿素肽的布朗斯台德碱催化剂与（芳基磺酰基）乙腈结合使用作为乙腈阴离子的合成当量。该方法使人们能够以良好的收率和出色的对映选择性获得各种β-氨基腈，并拓宽了可用于合成的立体选择性曼尼希型方法。
• Application of carbodiimide mediated Lossen rearrangement for the synthesis of α-ureidopeptides and peptidyl ureas employing N-urethane α-amino/peptidyl hydroxamic acids
  作者：N. Narendra、Gundala Chennakrishnareddy、Vommina V. Sureshbabu

  DOI：10.1039/b905790k

  日期：——

  Application of the Lossen rearrangement to the synthesis of N-urethane protected α-peptidyl ureas and ureidopeptides is reported. The carbodiimide mediated rearrangement of N-Boc/Z/Fmoc protected α-amino/peptide hydroxamic acids into isocyanates and coupling of the latter with the amino acid esters/peptide esters have been accomplished in a single-pot to obtain good yields of urea products. Synthesis

  报道了Lossen重排在N-氨基甲酸酯保护的α-肽基脲和脲肽的合成中的应用。这碳二亚胺N- Boc / Z / Fmoc保护的α-氨基/肽异羟肟酸介导的重排成异氰酸酯，后者与氨基酸酯/肽酯的偶联已在单罐中完成，从而获得了较高的收率。尿素产品。还已经使用相同的方法经由N-保护的天冬氨酸的异羟肟酸酯衍生物合成脲基丙氨酸衍生物。
• Synthesis of <i>N</i> ^{<font>α</font>}-Protected Amino Acid–Derived Selenocarbamates Employing Isocyanates as Key Intermediates
  作者：Vommina V. Sureshbabu、Shankar A. Naik

  DOI：10.1080/00397910903318641

  日期：2010.8.16

  A simple protocol for the synthesis of N-urethane-protected N-alkyl-Se-alkyl selenocarbamate derivatives of amino acids has been described. The reaction of N-urethane-protected amino alkyl isocyanates with selenating agent LiAlHSeH and subsequent coupling with an alkyl halide yielded the title compounds in good yield and purity. All the selenocarbamates obtained have been characterized by 1H NMR, 13C NMR, and mass spectral studies.
• Patil, Basanagoud S.; Vasanthakumar, Ganga-Ramu; Suresh Babu, Vommina V., Journal of Organic Chemistry, 2003, vol. 68, # 19, p. 7274 - 7280
  作者：Patil, Basanagoud S.、Vasanthakumar, Ganga-Ramu、Suresh Babu, Vommina V.

  DOI：——

  日期：——